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Diastereomeric Resolution of Racemic o ‐Chloromandelic Acid
Author(s) -
Wang Pei,
Zhang En,
Zhao Peng,
Ren QingHua,
Guan YuanYuan,
Liu HongMin
Publication year - 2012
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22089
Subject(s) - chemistry , diastereomer , enantiopure drug , chirality (physics) , yield (engineering) , propylamine , stereochemistry , resolution (logic) , enantiomer , salt (chemistry) , medicinal chemistry , organic chemistry , catalysis , amine gas treating , enantioselective synthesis , nambu–jona lasinio model , chiral symmetry breaking , physics , materials science , quantum mechanics , quark , artificial intelligence , computer science , metallurgy
ABSTRACT The separation of rac‐o ‐chloromandelic acid 1 with enantiopure aryloxypropylamine via diastereomeric salt formation was investigated. ( R )‐ o ‐chloromandelic acid ( R )‐ 1 , a key intermediate for the antithrombotic agent clopidogrel, was obtained in 65% yield and 98% ee by Dutch resolution of rac ‐ 1 with ( S )‐2‐hydroxyl‐3‐( p ‐chlorophenoxy) propylamine ( S )‐ 5 as resolving agent and ( S )‐2‐hydroxyl‐3‐( o ‐nitrophenoxy) propylamine ( S )‐ 4 as nucleation inhibitor. Chirality 24:1013–1017, 2012 . © 2012 Wiley Periodicals, Inc.