Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (4): 1123-1128.DOI: 10.6023/cjoc202112007 Previous Articles     Next Articles



韩群, 徐坤*(), 田发宁, 黄胜阳*(), 曾程初*()   

  1. 北京工业大学环境与生命学部 北京 100124
  • 收稿日期:2021-12-03 修回日期:2021-12-30 发布日期:2022-01-11
  • 通讯作者: 徐坤, 黄胜阳, 曾程初
  • 基金资助:
    国家自然科学基金(21871019); 北京工商大学北京市食品风味化学重点实验室开放课题基金资助项目(BTBU)

A Practical Transamidation Strategy for the N-Deacylation of Amides

Qun Han, Kun Xu(), Faning Tian, Shengyang Huang(), Chengchu Zeng()   

  1. Faculty of Environment and Life, Beijing University of Technology, Beijing 100124
  • Received:2021-12-03 Revised:2021-12-30 Published:2022-01-11
  • Contact: Kun Xu, Shengyang Huang, Chengchu Zeng
  • Supported by:
    National Natural Science Foundation of China(21871019); Open Project Program of Beijing Key Laboratory of Flavor Chemistry, Beijing Technology and Business University(BTBU)

The N-deacylation of amides under mild conditions is highly desirable in organic synthesis, but it remains challenging due to the chemically robust nature of amide bond. A general solution to the N-deacylation of amides with NH3•H2O under mild and scalable conditions (10 mmol) was developed. A range of drugs and drug derivatives including indomethacin, N-acetyl melatonin and N-acetyl carprofen could be deacylated to release free amines in excellent yields. The good functional group compatibility, combined with operational simplicity, excellent yield and cost effectiveness of all reagents, makes this protocol a prime candidate for N-deacylation of amide.

Key words: deacylation, transamidation, green synthesis, amide