RAVUCONAZOLE

Ravuconazole

BMS-207147, ER-30346

• BMS 207147
• ER 30346
• Ravuconazole
• UNII-95YH599JWV

CAS Registry Number: 182760-06-1

CAS Name: 4-[2-[(1R,2R)-2-(2,4-Difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-4-thiazolyl]benzonitrile

Additional Names: (2R,3R)-3-[4-(4-cyanophenyl)thiazol-2-yl]-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol

(2R,3R)-3-i4-(4-cvanophenyl)thiazol-2-yl1-1 -(1 H-1 ,2,4-triazol-1 -yl)-2-(2,4-difluorophenyl)- butan-2-ol

 [R-(R*,R*)]-4-[2-[2-(2,4-Difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-4-thiazolyl]benzonitrile
4-[2-[(1R,2R)-2-(2,4-Difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-4-thiazolyl]benzonitrile

Molecular Formula: C22H17F2N5OS

Molecular Weight: 437.47

Percent Composition: C 60.40%, H 3.92%, F 8.69%, N 16.01%, O 3.66%, S 7.33%

Eisai (INNOVATOR)

Properties: Colorless prisms from diisopropyl ether/n-hexane, mp 164-166°. [a]D24=  -29.1° (c = 1.03 in methanol).

Melting point: mp 164-166°

Optical Rotation: [a]D24=  -29.1° (c = 1.03 in methanol)

Therap-Cat: Antifungal.

http://www.google.com/patents/WO2011042827A1?cl=en…………

m.p. 164-166° C; [a]=-30° (c=1 , methanol, 25° C); 

NMR (CDCI3): 1 .23(3H, d, J=8 Hz), 4.09(1 H, q, J=8Hz), 4.26(1 H, d, J=14Hz), 4.92(1 H, d, J=14Hz), 5.75(1 H, s), 6.75- 6.85(2H, m), 7.45-7.54(2H, m), 7.62(1 H, s), 7.69(1 H, s), 7.75(1 H, d, J=8Hz), 7.86(1 H, s), 8.03(1 H,d,J=8Hz). 

The analytical data were identical with published (US5648372 and Chem. Pharm. Bull. 1998, 46, 623-630).

1H NMR PREDICT

13 C NMR PREDICT

Improved Chiral Synthesis of Ravuconazole - Taylor ...
www.tandfonline.com/doi/pdf/10.1080/00397910802563420
by L Xu - ‎2009 - ‎Cited by 6 - ‎Related articles
developed also a new convergent synthesis of ravuconazole.[7] The key step of this ... electivity (determined by NMR to be 16:1) seemed better. As expected, the  ...

 4-[2-[2(R)-(2,4-difluorophenyl)-2-hydroxy-1(R)- methyl-3-(1,2,4-triazol-1-yl)propyl]thiazol-4-yl]benzonitrile (ravuconazole) (0.11 g, 0.25 mmol, yield: 79.5%). White solid; melting point: 161.6 to 163 C. Enantiomeric excess: >99.5% as determined by HPLC on Chiralpak AD-H column [n-hexane (0.1% TFA)=ethanol].

[a]D 20¼ 30.2 (c ¼ 1, MeOH).

IR (KBr): 2226, 1608, 1500, 1138 cm1 .

1 H NMR (DMSO-d6) d: 8.41 (s, 1 H), 8.20 (s, 1 H), 8.18 (d, J ¼ 8.4 Hz, 2 H), 7.91 (d, J ¼ 8.4 Hz, 2 H), 7.61 (s, 1 H), 7.26–7.30 (m, 1 H), 7.18– 7.23 (m, 1 H), 6.91–6.95 (m, 1 H), 6.07 (s, 1 H), 4.85 (d, J ¼ 14.4 Hz, 1 H), 4.35 (d, J ¼ 14.4 Hz, 1 H), 4.07 (q, J ¼ 7.2 Hz, 1 H), 1.12 (d, J ¼ 7.2 Hz, 3 H).

13C NMR (DMSO-d6) d: 172.45, 162.57 (dd, 1 JCF ¼ 245 Hz, 3 JCF ¼ 12.1 Hz), 159.33 (dd, 1 JCF ¼ 245 Hz, 3 JCF ¼ 12.1 Hz), 152.02, 151.12, 138.99, 145.41, 133.58, 130.90, 127.39, 125.30 (d, 2 JCF ¼ 14 Hz), 119.61, 119.09, 111.57 (d, 2 JCF ¼ 19.7 Hz), 110.78, 104.70 (d, 3 JCF ¼ 6 Hz), 76.89 (d, 2 JCF ¼ 26.6 Hz), 56.64, 45.21,17.25.

MS (API-ES) m=z 438.0.
Anal. calcd. for C22H17F2 N5OS: C, 60.40; H, 3.92; F, 8.69; N, 16.01; S, 7.33. Found: C, 60.56; H, 3.93; F, 8.76; N, 15.76; S, 7.36. AC

 Lin Xu , Marc R. Muller , Xiong Yu & Bao-Quan Zhu (2009) Improved Chiral Synthesis of Ravuconazole, Synthetic Communications: An International Journal for Rapid Communication of Synthetic Organic Chemistry, 39:9, 1611-1625, DOI: 10.1080/00397910802563420

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