Preparation of (S)-Clopidogrel and related compounds

Details Preparation of (S)-Clopidogrel and related compounds Preparation of (S)-Clopidogrel and related compounds

2005-02-22

2005-02-22

Desai, Rita (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C514S301000

Reexamination Certificate

active

06858734

ABSTRACT:
A process for producing enantiomerically enriched (S)-α-(2-chlorophenyl)-6,7-dihydrothieno[3,2-c]pyridine-5 (4H)-acetic acid hydrocarbyl ester, represented by the formula:Is provided, wherein R1and R2are hydrogens and R3is methyl (i.e., (S)-Clopidogrel). The process includes the steps of: (a) contacting N-2-chlorobenz-aldehyde-ylidene-1-ethylamine-2(2-thiophenyl)imine and an HCN source, in the presence of a non-metallic asymmetric Strecker catalyst to form enantiomerically enriched (S)-α,α-(2-thiophenylethylamino)(2-chlorophenyl)acetonitrile; (b) contacting the enantiomerically enriched (S)-α,α-(2-thiophenylethylamino)(2-chlorophenyl)acetonitrile and a formaldehyde equivalent, in the presence of an acid catalyst to form enantiomerically enriched α-5(4,5,6,7-tetrahydro[3,2-c]thienopyridyl)(2-chlorobenzyl)-nitrile; and (c) contacting the enantiomerically enriched α-5(4,5,6,7-tetrahydro[3,2-c]thienopyridyl)(2-chlorobenzyl)-nitrile and a reagent capable of converting a cyano group into an ester group to form enantiomerically enriched hydrocarbyl ester of (S)-α-(2-chlorophenyl)-6,7-dihydrothieno-[3,2-c]pyridine-5(4H)-acetic acid.

REFERENCES:
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patent: 2 769 313 (1997-10-01), None
Vachal et al. “Enantioselective catalytic addition of HCN to ketoimines. Catalytic synthesis of quaternary amono acids.” Org. Lett., vol. 2, No. 6, 2000, pp. 867-870 & S-1-S-32 (Supporting Information).

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