Preparation of Optically Active Succinic Acid Derivatives. II. Efficient and Practical Synthesis of KAD-1229

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概要

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• For large-scale synthesis of monocalcium bis[(2S)-2-benzyl-3-(cis-hexahydroisoindolin-2-ylcarbonyl)propionate]dihydrate (1,KAD-1229), we investigated regioselective reactions of (S)-2-benzylsuccinic acid (2) with cis-hexahydroisoindoline (4). It was difficult to obtain a half amide regioselectively through coupling reaction of the (S)-acid 2 with the amine 4. Therefore, the succinic acid 2 was converted to bis-activated esters 3a-c and these were reacted with 4 to give the amides 5a-c in good yields, regioselectively. The amides 5a-c were derived to KAD-1229,which has a potent hypoglycemic effect, in good yields.

• 公益社団法人日本薬学会の論文
• 1998-02-15

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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