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Showing posts with label FLOW SYNTHESIS. Show all posts
Showing posts with label FLOW SYNTHESIS. Show all posts

Thursday, 31 January 2019

Telescoped Sequence of Exothermic and Endothermic Reactions in Multistep Flow Synthesis

Abstract Image
A multistep sequential flow synthesis of isopropyl phenol is demonstrated, involving 4-step exothermic, endothermic, and temperature sensitive reactions such as nitration, reduction, diazotization, and high temperature hydrolysis. Nitration of cumene with fuming nitric acid produces 2- and 4-nitrocumene which are converted into respective cumidines by the hydrogenation using Pd/Ni catalyst in H-cube with gravity separation. Hydrolysis of in situ generated diazonium salts in the boiling acidic conditions is carried out using integration of flow and microwave-assisted synthesis. 58% of 4-isopropyl phenol was obtained. The sequential flow synthesis can be applied to synthesize other organic compounds involving this specific sequence of reactions.

Telescoped Sequence of Exothermic and Endothermic Reactions in Multistep Flow Synthesis

Chemical Engineering & Process Development DivisionCSIR-National Chemical LaboratoryDr. Homi Bhabha Road, Pune 411008, India
Org. Process Res. Dev., Article ASAP
DOI: 10.1021/acs.oprd.8b00008
*Phone: +91-20-25902153, E-mail: aa.kulkarni@ncl.res.in.
Amol A. Kulkarni
Dr.Amol A. Kulkarni
Chemical Engineering & Process Development
CSIR-National Chemical Laboratory
Dr. Amol A. Kulkarni is a Scientist in the Chemical Engineering Division at the National Chemical Laboratory. He did his B. Chem. Eng. (1998), M. Chem. Eng (2000) and Ph.D. in chemical engineering (2003) all from the University Dept. of Chem. Technology (UDCT, Mumbai). In 2004 he worked at the Max Planck Institute-Magdeburg (Germany) as a Alexander von Humboldt Research Fellow. At NCL he is driving a research program on the design of microreactors and exploring their applications for continuous syntheses including of nanoparticles. He has been awarded with the Max-Planck-Visiting Fellowship from the Max-Planck-Society, Munich for 2008-2011. His research areas include: (i) design and applications of microreactors, (ii) design of multiphase reactors, (iii) experimental and computational fluid dynamics, and (iv) nonlinear dynamics of coupled systems. He is an active member of Initiative for Research and Innovation in Science (IRIS) supported by Intel’s Education Initiative to organize National Science Fair and popularize science in India.

Image result for Yachita Sharma ncl pune

Yachita Sharma
Location Pune, India
Yachita Sharma is a PhD student at CSIR-National Chemical Laboratory, Pune (India). She received her MSc in Applied Organic Chemistry in 2010. Her work focuses on exploring the continuous flow synthesis involving exothermic reactions and their integration.
Image result for Yachita Sharma ncl pune
Arun Nikam
Location, Pune, India
Email: arun11nikam@gmail.com
Arun was born and raised in Koregaon, Maharashtra, India. He completed his bachelors and masters in chemical sciences from Shivaji Unversity, Kolhapur, India. Currently, He is pursuing his Ph. D. under the supervision of Dr. Amol A. Kulkarni and Dr. B. L. V. Prasad. His work mainly focuses on flow synthesis of nanoparticles, drug formulation, and polymers. He develops new synthesis procedures and translates into flow chemistry to increase productivity with excellent control over the quality of the product. He is also exploring the application of nanoparticles in catalysis, electronics and pharmaceutical fields. He specializes in microwave-assisted continuous flow synthesis of nanomaterial and organic intermediate. Apart from his research, he actively pursues Yoga and spirituality. He also likes to play volleyball and has competed in inter CSIR tournaments.

/////////isopropyl phenol, flow chem,

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Wednesday, 27 September 2017

Photochemical intramolecular amination for the synthesis of heterocycles

Green Chem., 2017, Advance Article
DOI: 10.1039/C7GC02261A, Communication
Shawn Parisien-Collette, Corentin Cruche, Xavier Abel-Snape, Shawn K. Collins
Polycyclic heterocycles can be formed in good to excellent yields via photochemical conversion of the corresponding substituted aryl azides under irradiation with purple LEDs in a continuous flow reactor.

Photochemical intramolecular amination for the synthesis of heterocycles

 Author affiliations


Polycyclic heterocycles can be formed in good to excellent yields via photochemical conversion of the corresponding substituted aryl azides under irradiation with purple LEDs in a continuous flow reactor. The experimental set-up is tolerant to UV-sensitive functional groups while affording diverse carbazoles, as well as an indole and pyrrole framework, in short reaction times. The photochemical method is presumed to progress through a mechanism differing from the other methods of azide activation involving transition metal catalysis.
Methyl 9H-carbazole-2-carboxylate (9): Following the Photodecomposition Procedure A, starting from Methyl 2’-azido-[1,1’-biphenyl]-4-carboxylate, the crude mixture was purified by silica gel column chromatography (100 % hexanes → 10 % ethyl acetate in hexanes), to afford the desired product as a white solid (24.3 mg, 72 % yield). Following the Photodecomposition Procedure B, starting from Methyl 2’-azido-[1,1’- biphenyl]-4-carboxylate, the crude mixture was purified by silica gel column chromatography (100 % hexanes → 10 % ethyl acetate in hexanes), to afford the desired product as a white solid (27.7 mg, 82 % yield). NMR data was in accordance with what was previously reported.16
16 Takamatsu, K.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2014, 16, 2892-2895


STR2 str3
4-Isopropyl-9H-carbazole (14): Following the Photodecomposition Procedure A, starting from 2-azido-2’-isopropyl-1,1’-biphenyl, the crude mixture was purified by silica gel column chromatography (100 % hexanes → 10 % ethyl acetate in hexanes), to afford the desired product as a yellow solid (16.6 mg, 53 % yield). Following the Photodecomposition Procedure B, starting from 2-azido-2’-isopropyl-1,1’-biphenyl and using ethyl acetate as the solvant, the crude mixture was purified by silica gel column chromatography (100 % hexanes → 10 % ethyl acetate in hexanes), to afford the desired product as a yellow solid (16.0 mg, 51 % yield).
1H NMR (400 MHz, DMSO-d6) δ = 11.29 (s, 1H), 8.11 (d, J = 8.1 Hz, 1H), 7.50 (d, J = 8.1 Hz, 1H), 7.39-7.31 (m, 3H), 7.19- 7.15 (m, 1H), 7.08-7.03 (m, 1H), 3.92-3.82 (m, 1H), 1.41 (d, J = 6.8 Hz, 6H);
13C NMR (100 MHz, DMSO-d6) δ = 143.9, 140.3, 140.1, 126.0, 125.2, 122.8, 122.2, 119.9, 119.1, 114.9, 111.2, 108.9, 30.2, 22.8 (2C);
HRMS (ESI) m/z calculated for C15H15N [M-H]- 208.1130; found 208.1126.

Wednesday, 21 December 2016

Synthesis of cyclic organic carbonates via catalytic oxidative carboxylation of olefins in flow reactors

Synthesis of cyclic organic carbonates via catalytic oxidative carboxylation of olefins in flow reactors
Catal. Sci. Technol., 2017, Advance Article
DOI: 10.1039/C6CY01974A, Paper
Ajay A. Sathe, Anirudh M. K. Nambiar, Robert M. Rioux
The direct catalytic conversion of olefins into cyclic carbonates using peroxide and carbon dioxide is demonstrated using continuous flow reactors.

Synthesis of cyclic organic carbonates via catalytic oxidative carboxylation of olefins in flow reactors

*Corresponding authors
aDepartment of Chemistry, The Pennsylvania State University, University Park, USA
E-mail: rioux@engr.psu.edu
Fax: 814 865 7846
Tel: 814 867 2503
bDepartment of Chemical Engineering, The Pennsylvania State University, University Park, USA
Catal. Sci. Technol., 2017, Advance Article
DOI: 10.1039/C6CY01974A

Methodology for direct catalytic conversion of olefins into cyclic carbonates using peroxide and carbon dioxide under relatively mild conditions is demonstrated. The protocol utilizes packed bed flow reactors in series to couple rhenium catalyzed olefin epoxidation and aluminum catalyzed epoxide carboxylation in a single sequence.

Thursday, 11 August 2016

Synthesis of a Precursor to Sacubitril Using Enabling Technologies

Abstract Image
An efficient preparation of a precursor to the neprilysin inhibitor sacubitril is described. The convergent synthesis features a diastereoselective Reformatsky-type carbethoxyallylation and a rhodium-catalyzed stereoselective hydrogenation for installation of the two key stereocenters. Moreover, by integrating machine-assisted methods with batch processes, this procedure allows a safe and rapid production of the key intermediates which are promptly transformed to the target molecule (3·HCl) over 7 steps in 54% overall yield.
Synthesis of a Precursor to Sacubitril Using Enabling Technologies

Continuous flow methodologyhas been used to enhance several steps in the synthesis of a precursor to Sacubitril.
In particular, a key carboethoxyallylation benefited from a reducedprocessing time and improved reproducibility, the latter attributable toavoiding the use of a slurry as in the batch procedure. Moreover, in batchexothermic formation of the organozinc species resulted in the formation ofside products, whereas this could be avoided in flow because heat dissipationfrom a narrow packed column of zinc was more efficient

Synthesis of a Precursor to Sacubitril Using Enabling Technologies

 Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, U.K.
 Novartis Pharma AG, Postfach, 4002 Basel, Switzerland
Org. Lett.201517 (21), pp 5436–5439
DOI: 10.1021/acs.orglett.5b02806, http://pubs.acs.org/doi/10.1021/acs.orglett.5b02806
*E-mail: svl1000@cam.ac.uk.
LCZ696 (sacubitril/valsartan) is a first-in-class combination of the angiotensin II receptor-blocker valsartan and the neprilysin inhibitor sacubitril. A recent head-to-head comparison of LCZ696 with enalapril in a double-blind trial was stopped early because the boundary for an overwhelming benefit with LCZ696 was crossed.As a result of this, LCZ696 was reviewed under the FDA’s priority review program and was granted approval on the July 7, 2015 to reduce the risk of cardiovascular death and hospitalization for HF in patients with chronic HF (NYHA Class II–IV) and reduced ejection fraction.
LCZ696 is a complex aggregate comprised of the anionic forms of sacubitril and valsartan, sodium cations, and water molecules in the molar ratio of 1:1:3:2.5, respectively
(2R, 4S)-5-(4-biphenylyl)-4-amino-2-methylpentanoic acid ethyl ester hydrochloride 3
To a stirred solution of (2R, 4S)-5-(4-Biphenylyl)-2-methyl-4-(tert-butylsulfinylamino)valeric acid 14 (50.0 mg, 134 μmol) in absolute ethanol (0.4 mL) at 0 °C was added thionyl chloride (20 μL, 268 μmol). The reaction mixture was stirred at room temperature for 3 h. The solvent was removed to yield 46.0 mg (99%) of titled compound 3 as a white solid.
1 H NMR (600 MHz, DMSO-d6) δ 8.17 (br. s, 3H), 7.66 (dd, J = 8.0, 7.4 Hz, 4H), 7.47 (t, J = 7.7 Hz, 2H), 7.36 (2 H, t, J = 7.4 Hz, H15, 2H), 7.36 (1 H, d, J = 8.0 Hz, H15), 3.99 (q, J = 7.1 Hz, H18), 3.42 – 3.36 (m, H4, 1H), 3.04 (dd, J = 13.8, 5.5 Hz, 1H), 2.81 (dd, J = 13.8, 8.1 Hz, 1H), 2.77 – 2.70 (m, 1H), 1.86 (ddd, J = 14.3, 9.1, 5.0 Hz, 1H), 1.59 (ddd, J = 13.8, 8.1, 5.4 Hz, 1H), 1.10 (t, J = 7.1 Hz, 3H), 1.07 (d, J = 7.1 Hz, 3H).
13C NMR (151 MHz, CDCl3) δ 174.7, 139.7, 138.7, 135.5, 130.0, 129.0, 127.4, 126.8, 126.5, 60.1, 50.4, 38.1, 35.5, 35.0, 17.5, 13.9.
HRMS (ESI+ , m/z [M+H]+ ) Calcd for C20H26NO2 312.1964; found 312.1967;
HPLC. 97:3 d.r. (Daicel Chiralpak AD-H column; isocratic n-hexane/ethanol/methanol/trimethylamine 80/10/10/0.2; 40 o C; flow rate = 0.8 mL min-1 ; λ = 254 nm; run time = 23 mins; tR (2R, 4S) 97.07%; tR (2S,4R) 0.21%; tR (2S, 4S) 2.32%; tR (2R,4R) 0.40%)

13C NMR Ethyl (2R,4S)-5-(4-biphenylyl)-4-amino-2-methylpentanoate hydrochloride 3
str2 str1
////////////Synthesis, Precursor,  Sacubitril, Enabling Technologies, flow synthesis, valsartan, LCZ69

Thursday, 15 October 2015

Multistep Flow Synthesis of 5-Amino-2-aryl-2H-[1,2,3]-triazole-4- carbonitrilesultistep Flow Synthesis of 5-Amino-2-aryl-2H-[1,2,3]-triazole-4- carbonitriles

Using the Uniqsis FlowSyn flow chemistry system researchers from the UCB Biopharma. Belgium have developed a flow synthesis of 2-substituted 1,2,3-triazoles that demonstrates improvements over the conventional batch route.
The route involves the diazotisation of anilines and condensation with malononitrile followed by the nucleophilic addition of ammonia or an alkylamine and finally a novel copper catalysed cyclisation. The intermediate azide was generated and consumed in situ which enabled safe scale up under the flow-through conditions employed.
DOI: 10.1002/chem.201402074

Multistep Flow Synthesis of 5-Amino-2-aryl-2H-[1,2,3]-triazole-4-carbonitriles

Authors, Dr. Jérôme Jacq, Dr. Patrick Pasau

Corresponding author
  1. UCB Biopharma, Avenue de l'Industrie, 1420 Braine l'Alleud (Belgium)
  • UCB Biopharma, Avenue de l'Industrie, 1420 Braine l'Alleud (Belgium)===
1,2,3-Triazole has become one of the most important heterocycles in contemporary medicinal chemistry. The development of the copper-catalyzed Huisgen cycloaddition has allowed the efficient synthesis of 1-substituted 1,2,3-triazoles. However, only a few methods are available for the selective preparation of 2-substituted 1,2,3-triazole isomers. In this context, we decided to develop an efficient flow synthesis for the preparation of various 2-aryl-1,2,3-triazoles. Our strategy involves a three-step synthesis under continuous-flow conditions that starts from the diazotization of anilines and subsequent reaction with malononitrile, followed by nucleophilic addition of amines, and finally employs a catalytic copper(II) cyclization. Potential safety hazards associated with the formation of reactive diazonium species have been addressed by inline quenching. The use of flow equipment allows reliable scale up processes with precise control of the reaction conditions. Synthesis of 2-substituted 1,2,3-triazoles has been achieved in good yields with excellent selectivities, thus providing a wide range of 1,2,3-triazoles.http://onlinelibrary.wiley.com/wol1/doi/10.1002/chem.201402074/full
1H/13c NMR OF 1a



UCB Biopharma,  Belgium

Uniqsis FlowSyn

Uniqsis Ltd
29 Station Road
+44 (0)845 864 7747

Map of cambridgeshire

Halifax survey names South Cambridgeshire as best place to live in rural Britain

///////////FLOW SYNTHESIS, UCB Biopharma, Belgium, Uniqsis FlowSyn

Mumbai Foods

10 Best Regional Foods you must Try in Mumbai!

1. The Street Food

10 Best Regional Foods you must Try
From Paav Bhaji, Vada Paav, potato and onion Bhajias, Bombay sandwiches, street-sideDosas, Patti Samosas, Pani Puri, Sev Puri, Dahi Puri, Ragda Pattis, boiled Channa Chaat,Kala Khatta, raw mango slices and berries in Chinese Bhel Indian-style pizzas heaped with cheese to fresh fruit accompanied by real dairy cream that is rare to find in most places. This is a gastronomes delight. As layers of flavours, textures, colours create dishes that pop in your mouth and hardly impact your pocket, it maybe fun to play a guessing game of what came from where and how it may have transformed here.
Where – In South Mumbai, Girgaum Chowpatty snack shops, Bachelors for shakes, Indian style pizzas and sandwiches, and Homji Street Khao Galli (Fort) offer a spectrum of street food. Cannon (near CST) and Sardar (Tardeo) are famous for Pao Bhaji, Gurukrupa (Sion) for Samosa Ragda and Haj Ali Juice Centre for fresh juices, fruit cream, sandwiches and Indian style pizzas.

2. A Konkani Coastal Meal

10 Best Regional Foods you must Try
The Konkan coast starts from Mumbai and goes on till Goa. Malvani cuisine is marked by the use of garam masala and red chilli. On the other hand, Gomantak cuisine is the coastal cuisine of areas in and around Goa and is marked by the generous use of fresh coconut and kokum. In most Mumbai restaurants, you’ll find a mix of Malvani and Gomatak cuisines. The curries here are tangy, coconut-y, fiery with spice and red chilli and accompanied by rice as the primary starch. Eat the catch of the day in a coconut-y curry poured over a heap of steaming white rice or mop them up with the variety of breads unique to this coast.

Where – Satkar (near Goregaon station) for Malvani, Highway Gomantak (on the Western Express Highway, Bandra East) and Goa House (Juhu), Singhudurg and Pradeep Gomatak (Fort).

3. A Typical Vegetarian Maharashtrian Meal

10 Best Regional Foods you must Try
The star attractions that really pull crowds are snacks like Thaali Peeth (a sort of a multigrain pancake or flatbread), Kandha Pohe (flattened rice snack), Sabudana Vada(sago and potato fritter flecked with roasted peanuts), Misal Paav (a fiery curry made of pulses and fried nothings served with bun), Kothimbir Vadi (coriander leaf and gram flour fritters) etc. Aamras (fresh mango puree) when in season and Kharwas (a jelly like milky pudding made from the milk of a cow that has just given birth) round off the meal perfectly.
Where: Aaswad (opposite Sena Bhavan in Dadar) and Prakash (Dadar) though Vinay Health Home (Charni Road) comes highly recommended as well.

4. A South Indian Meal

10 Best Regional Foods you must Try
The saga of Udupi cuisine began in this city when Rama Nayak arrived from Karnataka, in the 1940s. In Matunga, the area where a lot of South Indians lived, he set up his establishment near the King Circle railway station, and started cooking and serving authentic Udupi food on plantain leaves. This was Mumbai’s humble initiation into the idli-dosai menu. Soon Rama Nayak quadrupled his outlets into restaurants that are still known for great, uncompromising South Indian food in the city. Meanwhile, many other similar stories resulted in Udupi and Udupi-esque restaurants that cropped up all over the city, to be the primary dining room for the hungry working class of Mumbai.

Where: Most Udupi style restaurants have gotten Mumbaified in their offerings but there still are a few in Matunga like Ramanayaks Udupi (the thaali is what this place is most famous for), Udupi Idli House (absolutely fantastic range of idlis, chutneys and unlimitedsambhar), Café Madras (recommend almost everything here but the Podi Upma and Ragi Dosa are favourites), Ramashray (great idlis and dosas) and Manis Lunch Home (known for the thaalis).

5. Bori Mohalla Food Trail

10 Best Regional Foods you must Try
It is said that Bohris are a Muslim business community who came from Gujarat and made great inroads into trade and commerce. The Muslim eat street of Mumbai, offers a cuisine distinct from other Mughal/Muslim cuisines of the country. While Mohammed Ali Road is famous for the food it offers for Iftar during Ramzan, Bohri Mohallah is the hidden gem of Mumbai that comes alive at dusk everyday, just as the evening prayers are being said at the Saifee mosque near by. In these gallis you will discover unique dishes of the Memon and Dawoodi Bohra inspired from regions as diverse as Surat, Delhi, Lucknow to United Kingdom, Malaysia, Iran, China and Yemen. Every kind of meat imaginable is on offer, cooked in myriad ways, served up as kebabs or in rich gravies. Breads range from naan to khamiri to fried paranthas and the murtabak like Baida Roti.

Where: Savoury – Sarvii Valibhai Payawal, Surti 12 Handi (Handi), Noor Mohamadi Hotel (Chicken Sanju Baba, the recipe for which was allegedly given to the hotel by Sanjay Dutt), Indian Hotel (kebabs and rolls), Mohammed Kareem Chana Masale Wala (Channa Masala).

6. An Irani Cafe for a Parsi Meal

10 Best Regional Foods you must Try
Irani cafes (Iranis were the second batch of Zoroastrians to come to India from Persia) today offer simple menus with signature Parsi dishes including Salli Boti (a fantastic dish of melting mutton in a beautifully caramalised gravy, topped with crunchy fried potato straws), Mutton Dhansak (meat cooked in a creamy gravy of lentils and spices), Kheema Ghotala (curried minced mutton with an egg scrambled in, served with paav for breakfast) all to be washed down with the syrupy raspberry soda.

Where: Kyani (near Metro cinema) and Yazdani Bakery, Ideal Corner, Jimmy Boy (try their new Parsi Wedding feast), Military Cafe (all in Fort), Britannia (personally, I am of the opinion that the Berry Pulav is hyped but it certainly has great appeal and the berries themselves are a lovely tart-sweet payoff). In the suburbs, I would highly recommend theSalli Boti at Ashmit’s Snack Shack (Bandra, Pali Junction).

7. A Mangalorean Meal

10 Best Regional Foods you must Try
The food along the west coast of India is a continuum of gradually  transforming flavours. As you reach Mangalore things start to get more meaty. The seafood and meat gravies including Ghassi (the most famous gravy of this region) are served up with the silky gossamer like Neer Dosa (thin rice pancakes). The coconut laden Sukkapreparations of mutton, squid or clams make for another brilliant combination with the soft Neer Dosas. Chicken Roti, another specialty of Mangalore is an intriguing dish of chicken curry with a roasted coconut gravy, served over crisp rice cracker ‘Kori Roti‘ that softens into a dosa on soaking up the chicken gravy.

Where: Apoorva (Fort) and Pratap Lunch Home (Fort) offer fantastic home-style food while Trishna (Fort) and Mahesh (Fort and Juhu) are more famous high end ones; great if you want to try crabs, jumbo prawns, lobster and pomfret in a tandoori masala or International sauces.

8. A Modern American/International Meal

10 Best Regional Foods you must Try
An experience of Mumbai food would be incomplete without including the modern American/Continental, trendy, upmarket but just about affordable restaurants that have cropped up all over the city. A trend spearheaded by the enduring Indigo Restaurant and Deli which has become an institution in itself, these restaurants are rapidly increasing in number, available now in almost every mall as well as peppered around major office areas.

Where: Indigo Deli branches around the city, Indigo Restaurant (Colaba) broke new ground a decade ago in offering five star quality contemporary international food at relatively affordable prices in restaurants around the city.

9. Mumbai’s Old School Bars

10 Best Regional Foods you must Try
While Mumbai, like other Indian cities has its share of international food to offer, your experience would be incomplete without a mention of its age old bars that attract tourists and city dwellers as much or maybe more for their ambiance and location as for the food. The food is a mix of ‘continental’ (Indianised grills, steaks, burgers, sandwiches, pastas) with the essential North Indian and Chinese thrown in for good measure. The colonial Parsi cafe meets old school 80’s pub meets dingy, overcrowded street-side restaurant ambiance of the ones in South Mumbai makes these almost into a right of passage for city new comers and college students.

Where: Leopold, Café Mondegar and Café Churchill all flank the Taj Mahal Hotel in Colaba. Totos Garage and Janata Bar are both in Bandra.

10. Regional Bests

10 Best Regional Foods you must Try
If you want to try seriously authentic versions of cuisines from parts of the country you have never been to before, the city does offer a few restaurants that just about manage to escape Mumbaification.
Where: Head to Bhojohori Manna (Oshiwara) for superlative home-style Bengali food, Punjab Grill (Juhu or Phoenix Mills) for fantastically authentic Punjabi fare. Soam (Girgaum) and Hiralal Kashidas (Girgaon) make fantastic Gujarati Undhiyo when the season is right. Deluxe (Fort) and Just Kerala (Andheri East) are known for their non-vegetarian Kerala meal, Chetna (Fort) for its Rajasthani thali and Maharaja Bhog (Goregaon, Inorbit Mall) for a Gujarati and Rajasthani melange.