rac-Clopidogrel Carboxylic Acid synthesis
- Product Name:rac-Clopidogrel Carboxylic Acid
- CAS Number:90055-55-3
- Molecular formula:C15H14ClNO2S
- Molecular Weight:307.8
324757-50-8
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Yield:90055-55-3 98.4%
Reaction Conditions:
Stage #1: clopidogrel carboxylatewith sodium hydroxide in water; for 18 h;
Stage #2: with acetic acid in water; pH=4 - 5;
Steps:
71
Example 71 Synthesis of (t)-(2-chlorophenyl)-(4,5,6,7-4H-thieno[3,2,-c]pyrid-5-yl) acetic acid (VI) The mixture of (R)-(2-chlorophenyl)-(4,5,6,7-4H-thieno- [3,2,-c]pyrid-5-yl) acetic acid (61g, 0.199mol), aqueous NaOH (40%, 360g) was refluxed for 18 h in a suitable reaction flask. The reaction solution was adjusted to pH 4-5 with acetic acid, and cooled with stirring to room temperature, After filtration and drying, (+-)-(2-chlorophenyl)-(4,5,6,7-4H-thieno[3,2,-c]pyrid-5-yl) acetic acid (VI) was obtained as white solid powder in ee=0% (60g, yield 98.4%). The obtained product was characterized with IR, MS and 1H NMR. IR (cm-1): 1650 (s, -C=O), 3400 (-OH). MS (m/z): 308.1 (M+H)+ 1H NMR (CDCl3): δ 7.2-7.9 (4H, m), 7.1 (1H, d), 6.6 (1H, d), 3.57, 3.67 (2H, d), 4.1 (2H, s), 3.3-3.4 (2H, s).
References:
EP1942110,2008,A1 Location in patent:Page/Page column 29
![4,5,6,7-Tetrahydrothieno[3,2,c] pyridine hydrochloride](/CAS/GIF/28783-41-7.gif)
![(+/-)-RAC-2-(2-CHLOROPHENYL)-(6,7-DIHYDRO-4H-THIENO[3,2-C]PYRIDIN-5-YL)ACETONITRILE](/StructureFile/ChemBookStructure8/GIF/CB9472615.gif)
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![Thieno[3,2-c]pyridine-5(4H)-acetic acid, α-(2-chlorophenyl)-6,7-dihydro-, ethyl ester](/CAS/20211123/GIF/90055-81-5.gif)
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