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有机化学
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有机化学 ›› 2006, Vol. 26 ›› Issue (07): 988-991. 上一篇    下一篇

研究简报

4-(4-{5-[(二苄胺基甲酰)-甲基]-2-庚基-4-羰基-噻唑-3}-丁基)苯甲酸的合成研究

张新歌，李朝兴*，张慧杰，汤宇，王瑱   

  1. (南开大学高分子化学研究所 天津 300071)
  • 收稿日期:2005-05-24 修回日期:2006-01-23 发布日期:2006-07-01
  • 通讯作者: 李朝兴

Synthesis of 4-(4-{5-[(Dibenzylcarbamoyl)-methyl]-2-heptyl-4-oxo-thiazolidin-3-yl}-butyl)-benzoic Acid

ZHANG Xin-Ge,LI Chao-Xing*,ZHANG Hui-Jie,TANG Yu,WANG Zhen   

  1. (1 Department of Chemistry, The Fourth Military Medical University, Xi'an 710032)
    (2 Department of Pharmacology, The Fourth Military Medical University, Xi'an 710032)
  • Received:2005-05-24 Revised:2006-01-23 Published:2006-07-01
  • Contact: LI Chao-Xing

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报道一个新型胰岛素增敏剂4-(4-{5-[(二苄胺基甲酰)-甲基]-2-庚基-4-羰基-噻唑-3}-丁基)苯甲酸的合成方法. 该化合物以对碘苯甲酸为原料, 经过羧基的保护、Heck反应、还原反应、Ing-Mnske反应、噻唑环合成、酰胺制备和羧酸保护基解除等一系列反应, 通过对反应条件的优化, 高产率合成4-(4-{5-[(二苄胺基甲酰)-甲基]-2-庚基-4-羰基-噻唑-3}-丁基)苯甲酸, 并对其中间体对碘苯甲酸叔丁酯的合成方法进行研究.

关键词: 4-羰基噻唑烷酮, 胰岛素增敏剂, 对碘苯甲酸叔丁酯, 合成

A novel class of chiral phase transfer catalysts was synthesized conveniently from cinchona alkaloids and 2-(chloromethyl)benzimidazole. Using these new catalysts (10 mol%), enantioselective alkylations of N-(diphenylmethylene)glycine tert-butyl ester were efficiently carried out with various alkyl halides, and the chemical yields were up to 85% with the ee of the products up to 95%.

Key words: chiral phase transfer catalyst, cinchona alkaloid, enantioselective alkylation