rac-Clopidogrel Carboxylic Acid synthesis

12synthesis methods

Product Name:rac-Clopidogrel Carboxylic Acid
CAS Number:90055-55-3
Molecular formula:C15H14ClNO2S
Molecular Weight:307.8

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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

29270-30-2 Synthesis