A Practical Transamidation Strategy for the N-Deacylation of Amides

doi:10.6023/cjoc202112007

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

ARTICLES

一种利用酰胺基转移反应脱除酰基保护基的实用方法

韩群, 徐坤^*(), 田发宁, 黄胜阳^*(), 曾程初^*()

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()

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)

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Abstract

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

Cite this article

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.

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Entry	Deviation from standard conditions	Yield/%
1	None	91
2	r.t.	68
3	60 ℃	90
4	DCM instead of MeOH	Trace
5	DCE instead of MeOH	Trace
6	THF instead of MeOH	Trace
7	MeCN instead of MeOH	47
8	EtOH instead of MeOH	67
9	1 mL MeOH	56
10	0.8 mL NH₃•H₂O	77
11	CH₃NH₂ instead of NH₃•H₂O	63

Entry	Deviation from standard conditions	Yield/%
1	None	91
2	r.t.	68
3	60 ℃	90
4	DCM instead of MeOH	Trace
5	DCE instead of MeOH	Trace
6	THF instead of MeOH	Trace
7	MeCN instead of MeOH	47
8	EtOH instead of MeOH	67
9	1 mL MeOH	56
10	0.8 mL NH₃•H₂O	77
11	CH₃NH₂ instead of NH₃•H₂O	63

一种利用酰胺基转移反应脱除酰基保护基的实用方法

A Practical Transamidation Strategy for the N-Deacylation of Amides

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