title: [Thromboxane synthetase inhibitors. II. Optical resolution of 4-[alpha-hydroxy-5-(1-imidazolyl)-2-methylbenzyl]-3,5-dimethylbenzo ic acid].
abstract: The optical resolution of racemic 4-[alpha-hydroxy-5-(1-imidazolyl)-2-methylbenzyl]-3,5-dimethylbenzoic acid (dl-I), a new potent and long lasting thromboxane synthetase inhibitor, was investigated. (S)-3-(3,5-Dinitrobenzoylthio)-2-methylpropionyl group was introduced to alpha-hydroxy moiety of methyl ester of dl-I by three steps of reaction to give the corresponding ester compound (VIa). Then, two diastereomers of VIa, alpha-VIa and beta-VIa, were separated by column chromatography using on silica gel. Alkaline hydrolysis of alpha-VIa and beta-VIa, followed by reactions with sodium ethylate gave optically pure sodium salts of (-)-I and (+)-I, respectively. The separative determination methods for the diastereomers of VIa, and for the enantiomers of the sodium salts of dl-I by high performance liquid chromatography were also established.
authors.forename: M
authors.initials: M
authors.lastname: Tsuruda
authors.forename: T
authors.initials: T
authors.lastname: Shiotsuki
authors.forename: T
authors.initials: T
authors.lastname: Matsumoto
authors.forename: T
authors.initials: T
authors.lastname: Oe
mesh_terms: D007093:Imidazoles / Q000494:pharmacology; D009904:Optical Rotation; D013930:Thromboxane-A Synthase / Q000037:antagonists & inhibitors*
chemical_list: D007093:Imidazoles; C049966:Y 20811; D013930:Thromboxane-A Synthase