Chinese Journal of Organic Chemistry >
A Practical Transamidation Strategy for the N-Deacylation of Amides
Received date: 2021-12-03
Revised date: 2021-12-30
Online published: 2022-01-11
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
Qun Han , Kun Xu , Faning Tian , Shengyang Huang , Chengchu Zeng . A Practical Transamidation Strategy for the N-Deacylation of Amides[J]. Chinese Journal of Organic Chemistry, 2022 , 42(4) : 1123 -1128 . DOI: 10.6023/cjoc202112007
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