Premium
Optical resolution and absolute configuration of a nonsteroidal antiinflammatory drug, 2‐(10,11‐Dihydro‐10‐oxodibenzo‐[ b , f ]thiepin‐2‐yl)propionic acid
Author(s) -
Yamamoto Masao,
Nohira Hiroyuki,
Masaki Mitsuo
Publication year - 1990
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.530020415
Subject(s) - chemistry , enantiomer , diastereomer , racemization , absolute configuration , ethylamine , resolution (logic) , crystallization , nonsteroidal , salt (chemistry) , chiral resolution , epimer , enantiomeric excess , chromatography , stereochemistry , medicinal chemistry , organic chemistry , enantioselective synthesis , catalysis , medicine , artificial intelligence , computer science , pharmacology
The title compound (±)‐1 (CN‐100) was efficiently resolved into a pair of enantiomers by fractional crystallization of the diastereomeric salts of (−)‐and (+)‐1‐phenylethylamine. The purity of the enantiomers was determined using the chiral cellulose column (CHIRALCEL OJ ® ) which allowed direct separation of the enantiomers. A separation factor (α) of 1.73 was obtained. X‐Ray crystallographic analysis of the (+)‐isomer [salt of (−)‐1‐(4‐bromophenyl)ethylamine] showed that this enantiomer has S‐configuration. Biological studies have shown that only the (+)‐isomer has antiinflammatory activity. Racemization of (−)‐isomer was carried out by heating its propionic acid solution in the presence of mineral acid, such as HBr.