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有机化学
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有机化学 ›› 2007, Vol. 27 ›› Issue (10): 1264-1267. 上一篇    下一篇

研究论文

(S)-N-Boc-α-氨基庚(辛)二酸单酯和双酯的制备

缪伟，徐卫良，张治柳，马汝建*，陈曙辉，李革   

  1. (药明康德新药开发有限公司 上海 200131)
  • 收稿日期:2007-01-22 修回日期:2007-03-08 发布日期:2007-09-28
  • 通讯作者: 马汝建

Synthesis of (S)-N-Boc-α-aminopimelic and (S)-N-Boc-α-aminosuberic Monoester and Diester

MIAO Wei,XU Wei-Liang,ZHANG Zhi-Liu
MA Ru-Jian*,CHEN Shu-Hui,LI Ge   

  1. (WuXi PharmaTech Co., Ltd., Shanghai 200131)
  • Received:2007-01-22 Revised:2007-03-08 Published:2007-09-28
  • Contact: MA Ru-Jian

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以(S)-N-Boc焦谷氨酸乙酯为原料, 经DIBAL-H还原得到半缩醛, 然后经Wittig反应得到相应的烯烃, 最后氢化制得(S)-N-Boc-α-氨基庚二酸二(单)酯, 总收率为85.1%(二酯)和86.1%(单酯). 另外, 以(S)-N-Boc-哌啶-2-甲酸为原料经酯化和氧化得内酰胺, 然后经还原、Wittig反应、氢化得到(S)-N-Boc-α-氨基辛二酸二(单)酯, 总收率为72.5%(二酯)和72.4%(单酯). 产品用1H NMR, MS表征.

关键词: (S)-N-Boc-α-氨基庚(辛)二酸酯, (S)-N-Boc-焦谷氨酸乙酯, 合成

A practical synthesis of (S)-N-Boc-α-aminopimelate starting from (S)-N-Boc-pyroglutamate in three steps including a reduction, a Wittig reaction and a hydrogenation with the overall yields of 85.1% (diester) and 86.1% (monoester) was developed. Meanwhile, a practical synthesis of (S)-N-Boc-α-aminosuberate starting from (S)-N-Boc-piperidine-2-carboxylic acid in five steps including an esterification, an oxygena-tion, a reduction, a Wittig reaction and a hydrogenation with the overall yields of 72.5% (diester) and 72.4% (monoester) was also developed.

Key words: (S)-N-Boc-α-aminosuberate, (S)-N-Boc-pyroglutamate, synthesis, (S)-N-Boc-α-aminopimelate