Preparation of Optically Active Succinic Acid Derivatives. I. Optical Resolution of 2-Benzyl-3-(cis-hexahydroisoindolin-2-ylcarbonyl)-propionic Acid

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概要

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• (+)-Monocalcium bis[(2S)-2-benzyl-3-(cis-hexahydroisoindolin-2-ylcarbonyl)propionate] dihydrate (KAD-1229,1) is an optically active succinic acid calcium salt derivative with potent hypoglycemic effect. We investigated two optical resolution methods. 2-Benzyl-3-(cis-hexahydroisoindolin-2-ylcarbonyl)propionic acid 6 was esterified with (S)-N-benzyl mandelamide and the resulting diastereomeric esters were separated by column chromatography on silica gel to give 7 and 8 in 39.1% and 45.3% yields, respectively. The diastereomer 7 was hydrolyzed to give the optically active acid (-)-6. The absolute configuration of (-)-6 was established as S by comparison with an authentic sample. The alternative method was resolution using an optically active amine. Treatment of a solution of the racemic acid 6 with 0.65 eq of (R)-1-(1-naphthyl)ethylamine in ethanol gave the salt in 23.2% yield with an optical purity of 96.8% ee.

• 公益社団法人日本薬学会の論文
• 1997-09-15

著者

• Yamaguchi Toshiaki

  Kissei Pharmaceutical Co. Ltd. Central Research Laboratories

• Yamaguchi Takuji

  Central Research Laboratory Tsumura & Co.

• YAMAMOTO IWAO

  Shinshu University

• YANAGI Takashi

  Kissei Pharmaceutical Co., Ltd., Central Research Laboratories

• HOKARI Hiroshi

  Kissei Pharmaceutical Co., Ltd., Central Research Laboratories

• MUKAIYAMA Yuko

  Kissei Pharmaceutical Co., Ltd., Central Research Laboratories

• KAMIJO Tetsuhide

  Kissei Pharmaceutical Co., Ltd., Central Research Laboratories

• KAMIJO Tetsuhide

  Central Research Laboratories, Kissei Pharmaceutical Co., Ltd.

• Yamaguchi T

  Tsumura Res. Laboratories Tsumura & Co.

• Yamamoto I

  Faculty Of Textile Science And Technology Shinshu University

• Hokari Hiroshi

  Kissei Pharmaceutical Co. Ltd. Central Research Laboratories

• Mukaiyama Yuko

  Kissei Pharmaceutical Co. Ltd. Central Research Laboratories

• Kamijo T

  Central Research Laboratories Kissei Pharmaceutical Co. Ltd.

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