Thromboxane合成酵素阻害剤(第2報)4-[α-Hydroxy-5-(1-imidazolyl)-2-methylbenzyl]-3,5-dimethylbenzoic Acidの光学分割

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The optical resolution of racemic 4-[α-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 α-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, α-VIa and β-VIa, were separated by column chromatography using on silica gel. Alkaline hydrolysis of α-VIa and β-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.
公益社団法人日本薬学会の論文
1989-01-25