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Showing posts with label nmr. Show all posts
Showing posts with label nmr. Show all posts

Monday, 10 December 2018

(1S,4R)-2-(4-Methoxybenzoyl)bicyclo[2.2.2]octa-2,5-diene

Capture


STR1 STR2
(1S,4R)-2-(4-Methoxybenzoyl)bicyclo[2.2.2]octa-2,5-diene (3a) Yellow liquid (25.2 mg, 95% yield):
1H NMR (300 MHz, CDCl3)   1.39 (s, 4H, alkyl), 3.77-3.80 (m, 1H, alkyl), 3.85 (s, 3H, OMe), 4.36 (d, J = 5.4 Hz, 1H, alkyl), 6.36 (dd, J = 6.0, 6.0 Hz, 1H, vinyl), 6.46 (dd, J = 6.0, 6.0 Hz, 1H, vinyl), 6.88-6.91 (m, 3H, vinyl + arom.), 7.67 (d, J = 8.3 Hz, 2H, arom.);
13C{1H} NMR (75 MHz, CDCl3)  = 24.7, 24.8, 37.1, 38.2, 55.4, 113.3, 130.8, 131.5, 133.2, 135.1, 146.5, 147.7, 162.6, 192.3;
HRMS (ESI-TOF) m/z calculated for C16H16NaO2 [M+Na]+ 263.1048, found 263.1036;
FT-IR (neat, cm-1 ) 1033, 1174, 1255, 1354, 1600, 1637, 1730, 2870, 2957, 3054.
Optical Rotation: []D 26 +39.9 (c 2.52, CHCl3) for an enantiomerically enriched sample of 94% ee.
HPLC analysis (column, CHIRALPAK AD-3, hexane/2-propanol = 98/2, flow rate 1.0 mL/min, 20 C, detection UV 250 nm light); tR of major-isomer 20.7
Org. Lett.201820 (23), pp 7353–7357
DOI: 10.1021/acs.orglett.8b02263
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(1S,4R)-2-(4-Methoxybenzoyl)bicyclo[2.2.2]octa-2,5-diene




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Sunday, 23 September 2018

3-fluoro-4- morpholinoaniline

STR1 STR2
3-fluoro-4- morpholinoaniline
1H NMR (400MHz, CDCl3)  6.82 (m, 1H, ArH), 6.43 (m, 2H, 2xArH), 3.87 (m, 4H, 2xCH2O), 3.58 (brs, 2H, NH2), 2.99 (m, 4H, 2xCH2N). 13C NMR (100MHz, CDCl3)  156.9 (d J= 245.4Hz), 143.0 (d J=10.4Hz), 131.8 (d J=9.7Hz), 120.4 (d J=4.2Hz), 110.8 (d J=3.0Hz), 104.0 (d J=23.8Hz), 67.3, 51.9 (d J=2.1Hz). HRMS [M] Calcd for C10H13FN2O 196.1006, Found 196.1004.
 
Org. Process Res. Dev., Article ASAP
DOI: 10.1021/acs.oprd.8b00153

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4-(2-fluoro-4-nitrophenyl)morpholine

str3 str4
4-(2-fluoro-4-nitrophenyl)morpholine
1H NMR (400MHz, CDCl3)  8.03 (ddd J=1.0, 2.6 and 9.0Hz, 1H, ArH), 7.94 (dd J=2.6 and 13.1Hz, 1H, ArH), 6.94 (t J=8.7Hz, 1H, ArH), 3.90 (t J=4.7Hz, 4H, 2xCH2O), 3.31 (m, 4H, 2xCH2N).
13C NMR (100MHz, CDCl3)  153.3 (d J=249.5), 145.6 (d J=7.8Hz), 121.1 (d J=3.0Hz), 117.0 (d J=3.9Hz), 112.7 (d J=6.4Hz), 66.7, 50.0 (d J=4.9Hz).
HRMS [M] Calcd for C10H11FN2O3 226.0748, Found 226.0749.

Catalytic Static Mixers for the Continuous Flow Hydrogenation of a Key Intermediate of Linezolid (Zyvox)

James GardinerXuan NguyenCharlotte GenetMike D. HorneChristian H. Hornung, and John Tsanaktsidis
 
Org. Process Res. Dev., Article ASAP
DOI: 10.1021/acs.oprd.8b00153
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Friday, 14 September 2018

1-(4-Cyanophenyl)piperazine


STR1

1-(4-Cyanophenyl)piperazine
1-(4-Cyanophenyl)piperazine (1a).1 Isolated as a mixture of mono (1a) and di (3) arylated products ~9:1. Conversion: quantitative. Peaks attributed to 1a: 1H NMR (400 MHz, CD3Cl) δH 7.47 (m, 2H, arH), 6.83 (m, 2H, ar-H), 3.26 (m, 4H, pip-H), 2.99 (m, 4H, pip-H), 1.69 (br s, 1H, NH). Peaks attributed to 3: 7.52 (d, J = 9.0 Hz, 4H, ar-H), 6.88 (d, J = 9.0 Hz, 4H, ar-H), 3.29 (s, 8H, pip-H).
Org. Process Res. Dev., Article ASAP
DOI: 10.1021/acs.oprd.8b00090
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Friday, 27 April 2018

Tert-butyl (N-[3-[(3S,4R)-3-amino-4-fluoro-4-(hydroxymethyl)tetrahydrofuran-3-yl]-4-fluorophenyl]acetamide)

STR1

tert-butyl (N-[3-[(3S,4R)-3-amino-4-fluoro-4-(hydroxymethyl)tetrahydrofuran-3-yl]-4-fluorophenyl]acetamide)

STR1
1H-NMR (500 MHz, DMSO-d6): 1.31 (s, 9H), 2.02 (s, 3H), 3.21 (m, 1H), 3.88 (m, 1H), 3.94 (m, 1H), 4.03 (m, 1H), 4.13 (m, 1H), 4.74 (m, 1H), 5.07 (m, 1H), 7.08 (m, 1H), 7.43 (bs, 1H), 7.63 (m, 1H), 7.67 (m, 1H), 10.03 (s, 1H) .
STR2
13C-NMR (125 MHz, DMSO-d6): 24.3, 28.5, 60.8, 65.1, 72.6, 78.1, 78.9, 105.8, 116.4, 119.7, 120.8, 127.2, 136.2, 155.2, 156.4, 168.7.
str3
19F-NMR (470.6 MHz, DMSO-d6): -164.77, -117.26.

str4 str5
Org. Process Res. Dev., Article ASAP
DOI: 10.1021/acs.oprd.8b00069

Tuesday, 27 March 2018

BRUSH UP YOUR NMR, 4-(3,5-Dichloropyridin-4-yl)morpholine

str1
3,5-Dichloro-4-morpholinopyridine
 
 5 as a light-orange solid.
 
1H NMR (CDCl3, 400 MHz): δ = 8.35 (2H, s), 3.84 (4H, m), 3.37 (4H, m);
 
13C NMR (CDCl3, 101 MHz): δ = 150.8, 149.3, 128.4, 67.4, 50.4;
 
HRMS–ESI+m/z [M + H]+ calcd for C9H11Cl2N2O+: 233.02429; found: 233.02446.
 
 
 
Org. Process Res. Dev., Article ASAP
DOI: 10.1021/acs.oprd.8b00009
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Clc2cncc(Cl)c2N1CCOCC1

Monday, 19 March 2018

S-Acetylation of Thiols Mediated by Triflic Acid: A Novel Route to Thioesters

Abstract Image
This paper demonstrates an efficient, mild, and chemoselective synthesis of various thioesters via a HOTf-catalyzed S-acetylation of aromatic and aliphatic thiols using isopropenyl acetate as a cheap and convenient acetylating agent. During our tests, we also investigated the differences between the activities of metal triflates and triflic acid as catalysts in the acetylation of thiols. Finally, the potential of our concept has been increased by the implementation of Nafion as a heterogeneous catalyst for S-acetylation of thiols.

S-Acetylation of Thiols Mediated by Triflic Acid: A Novel Route to Thioesters

Faculty of ChemistryAdam Mickiewicz University in Poznańul. Umultowska 89b, 61-614 Poznań, Poland
Org. Process Res. Dev., Article ASAP
DOI: 10.1021/acs.oprd.7b00378
Publication Date (Web): March 12, 2018
Copyright © 2018 American Chemical Society
 
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Friday, 9 March 2018

Concise synthesis of ketoallyl sulfones through an iron-catalyzed sequential four-component assembly

 
Green Chem., 2018, 20,973-977
DOI: 10.1039/C7GC03719H, Communication
Fuhong Xiao, Chao Liu, Dahan Wang, Huawen Huang, Guo-Jun Deng
A three starting material four component reaction (3SM-4CR) strategy is described to prepare [small beta]-acyl allylic sulfones from methyl ketones, sodium sulfinates and dimethylacetamide (DMA) in an iron-catalyzed oxidative system.

Concise synthesis of ketoallyl sulfones through an iron-catalyzed sequential four-component assembly

 
Author affiliations

Abstract

A three starting material four component reaction (3SM-4CR) strategy is described to prepare β-acyl allylic sulfones from methyl ketones, sodium sulfinates and dimethylacetamide (DMA) in an iron-catalyzed oxidative system. In this process, DMA was used as a dual synthon to provide two carbons. A broad range of functional groups were tolerated in this reaction system.
 1-phenyl-2-(tosylmethyl)prop-2-en-1-one (3ab)
 
43.2 mg, 72% yield).
 
1 H NMR (400 MHz, CDCl3) δ 7.78 (d, J = 8.2 Hz, 2H), 7.68-7.65 (m, 2H), 7.55 (t, J = 7.4 Hz, 1H), 7.43 (t, J = 7.8 Hz, 2H), 7.30 (d, J = 8.3 Hz, 2H), 6.25 (s, 1H), 6.02 (s, 1H), 4.35 (s, 2H), 2.39 (s, 3H).
 
13C NMR (100 MHz, CDCl3) δ 194.7, 144.9, 136.1, 135.8, 135.7, 133.9, 132.6, 129.8, 129.6, 128.3, 128.2, 57.7, 21.6.
 
HRMS calcd. for: C17H17O3S+ [M+H]+ 301.08929, found 301.08908
 
STR1 STR2

1H NMR PREDICT




13C NMR PREDICT ABOVE

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Cc1ccc(cc1)S(=O)(=O)CC(=C)C(=O)c2ccccc2

Thursday, 15 February 2018

p-Aminophenol

STR1 STR2
p-Aminophenol [123-30-8].
M.p. 182 °C; 1H NMR (300 MHz, d6-DMSO): 4.37 (br s, 2H, NH2), 6.37-6.44 (m, 2HAr), 6.44-6.50 (m, 2HAr), 8.33 (br s, 1H, OH);
13C NMR (75 MHz, d6-DMSO): δ 115.2 (2 CHAr), 115.5 (2 CHAr), 140.7 (Cq Ar), 148.2 (Cq Ar);
IR (ATR) max: 3338, 3279, 1471; MS (ESI+ ): 110.1 ([M+H]+ , 100).
1D 1H, 7.4 spectrum for 4-Aminophenol

1D 1H ABOVE


2D [1H,1H]-TOCSY, 7.4 spectrum for 4-Aminophenol

2D [1H,1H]-TOCSY ABOVE

1D 13C, 7.4 spectrum for 4-Aminophenol

1D 13C ABOVE


1D DEPT90, 7.4 spectrum for 4-Aminophenol

1D DEPT90 ABOVE

1D DEPT135, 7.4 spectrum for 4-Aminophenol

1D DEPT135 ABOVE

2D [1H,13C]-HSQC, 7.4 spectrum for 4-Aminophenol

2D [1H,13C]-HSQC ABOVE

2D [1H,13C]-HMBC, 7.4 spectrum for 4-Aminophenol

2D [1H,13C]-HMBC ABOVE