Diastereomeric Resolution of Racemic  o ‐Chloromandelic Acid | Zendy

Wang Pei | Zendy; Zhang En | Zendy; Zhao Peng | Zendy; Ren QingHua | Zendy; Guan YuanYuan | Zendy; Liu HongMin | Zendy

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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

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.

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