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有机化学
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有机化学 ›› 2006, Vol. 26 ›› Issue (12): 1692-1695. 上一篇    下一篇

研究简报

ω-苯基-(2S)-N-叔丁氧羰基氨基酸乙酯的制备

丁传勇a，马汝建b，荣国斌*,a   

  1. (a华东理工大学化学与制药学院 上海 200237)
    (b无锡药明康德新药开发有限公司 上海 200131)
  • 收稿日期:2005-01-18 修回日期:2006-05-27 发布日期:2006-11-21
  • 通讯作者: 荣国斌

Preparation of ω-Phenyl-2S-N-Boc-amino Acid Ethyl Ester

DING Chuan-Yonga,MA Ru-Jianb,RONG Guo-Bin*,a   

  1. (a Department of Chemistry and Pharmaceutics, East China University of Science and Technol-ogy, Shanghai 200237)
    (b Wuxi PharmaTech Co., Ltd., Shanghai 200131)
  • Received:2005-01-18 Revised:2006-05-27 Published:2006-11-21
  • Contact: RONG Guo-Bin

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格氏试剂和N-叔丁氧羰基焦谷氨酸乙酯反应生成中间体ω-苯基-δ-氧代-(2S)-N-叔丁氧羰基氨基酸乙酯, 分别用对甲基苯磺酰肼和醋酸硼氢化钠结合的一锅法还原或Pd/C催化氢化还原中间体得到ω-苯基-(2S)-N-叔丁氧羰基氨基酸乙酯.

关键词: 制备, N-叔丁氧羰基焦谷氨酸乙酯, ω-苯基-(2S)-N-叔丁氧羰基氨基酸乙酯

N-Boc-pyroglutamic ethyl ester was treated with Grignard reagents to afford ω-phenyl-δ- oxo-2S-N-Boc-amino acid ethyl esters, which were subsequently reduced either with one-pot reaction in the presence of TsNHNH2 and NaBH(OAc)3 or Pd/C catalyzed hydrogenation to yield the desired ω-phenyl-2S-N-Boc-amino acid ethyl esters.

Key words: preparation, N-Boc-pyroglutamic ethyl ester, ω-phenyl-2S-N-Boc-amino acid ethyl ester