Diastereomeric resolution of racemic o-chloromandelic acid.
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.
School of Pharmaceutical Sciences and New Drug Research & Development Center, Zhengzhou University, People's Republic of China.
Pei
P
Wang
En
E
Zhang
Peng
P
Zhao
Qing-Hua
QH
Ren
Yuan-Yuan
YY
Guan
Hong-Min
HM
Liu
D008333:Mandelic Acids / Q000737:chemistry* / Q000302:isolation & purification*; D011437:Propylamines / Q000737:chemistry; D013237:Stereoisomerism
C541344:2-chloromandelic acid; D008333:Mandelic Acids; D011437:Propylamines