An asymmetric synthesis of clopidogrel hydrogen sulfate was written by Sashikanth, Suthrapu;Raju, Veeramalla;Somaiah, Sripathi;Rao, Peddi Srinivasa;Reddy, Karnati Venugopal. And the article was included in Synthesis in 2013.Electric Literature of C9H10ClNO2 The following contents are mentioned in the article:
An asym. synthesis of (S)-(+)-clopidogrel hydrogen sulfate was developed through application of a Strecker reaction with [(1S)-1-(4-methoxyphenyl)ethyl]amine.HCl (I) as a chiral auxiliary. Addition of 2-ClC6H4CHO to a solution of NaCN and I gave diastereoisomerically pure (2S)-(2-chlorophenyl){[(1S)-1-(4-methoxyphenyl)ethyl]amino}acetonitrile.HCl. Cleavage of the chiral auxiliary and concomitant hydrolysis of the nitrile group then gave enantiomerically pure (2S)-2-(2-chlorophenyl)glycine.HCl, a key intermediate for (S)-(+)-clopidogrel. This study involved multiple reactions and reactants, such as (S)-Methyl 2-amino-2-(2-chlorophenyl)acetate (cas: 141109-14-0Electric Literature of C9H10ClNO2).
(S)-Methyl 2-amino-2-(2-chlorophenyl)acetate (cas: 141109-14-0) belongs to organic chlorides. Chlorinated organic compounds are found in nearly every class of biomolecules and natural products including alkaloids, terpenes, amino acids, flavonoids, steroids, and fatty acids.While alkyl bromides and iodides are more reactive, alkyl chlorides tend to be less expensive and more readily available. Alkyl chlorides readily undergo attack by nucleophiles.Electric Literature of C9H10ClNO2
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics