An Asymmetric Synthesis of Clopidogrel Hydrogen Sulfate

Abstract An asymmetric synthesis of ( S )-(+)-clopidogrel hydrogen sulfate has been developed through application of a Strecker reaction with [(1 S )-1-(4-methoxyphenyl)ethyl]amine hydrochloride as a chiral auxiliary. Addition of 2-chlorobenzaldehyde to a solution of sodium cyanide and [(1 S )-1-(4-...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2013-03, Vol.45 (5), p.621-624
Main Authors: Sashikanth, Suthrapu, Raju, Veeramalla, Somaiah, Sripathi, Rao, Peddi Srinivasa, Reddy, Karnati Venugopal
Format: Article
Language:English
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Summary:Abstract An asymmetric synthesis of ( S )-(+)-clopidogrel hydrogen sulfate has been developed through application of a Strecker reaction with [(1 S )-1-(4-methoxyphenyl)ethyl]amine hydrochloride as a chiral auxiliary. Addition of 2-chlorobenzaldehyde to a solution of sodium cyanide and [(1 S )-1-(4-methoxyphenyl)ethyl]amine hydrochloride­ gave diastereoisomerically pure (2 S )-(2-chlorophenyl){[(1 S )-1-(4-methoxyphenyl)ethyl]amino}acetonitrile hydro­chlor­ide. Cleavage of the chiral auxiliary and concomitant hydrolysis of the nitrile group then gave enantiomerically pure (2 S )-2-(2-chlorophenyl)glycine hydrochloride, a key intermediate for ( S )-(+)-clopidogrel.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0032-1316852