Selective N-debenzylation of amides with p-TsOH

Ching Yuh Chern; Yu Ping Huang; Wai Ming Kan

doi:10.1016/S0040-4039(02)02738-7

Selective N-debenzylation of amides with p-TsOH

Ching Yuh Chern
, Yu Ping Huang
, Wai Ming Kan

Department of Pharmacology

Research output: Contribution to journal › Article › peer-review

47 Citations (Scopus)

Abstract

N-Benzylamides were debenzylated efficiently with 4 equiv. of p-TsOH in refluxing toluene. Good to quantitative yields of the desired primary amides were obtained within 2-4 h from a wide variety of N-2,4-dimethoxybenzylamides. N-4-Methoxylbenzyl amides and N-benzylamides were also debenzylated cleanly. In the case of N-2,4-dimethoxylbenzylamides, selective N-debenzylation was possible in the presence of N-Fmoc, N-t-BOC or N-trityl-protection. Protected amino acid amides survived these conditions without any detectable epimerization.

Original language	English
Pages (from-to)	1039-1041
Number of pages	3
Journal	Tetrahedron Letters
Volume	44
Issue number	5
DOIs	https://doi.org/10.1016/S0040-4039(02)02738-7
Publication status	Published - 2003 Jan 27

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(02)02738-7

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@article{35e60cafa6ae4e4eaf40d0e7c88125b9,

title = "Selective N-debenzylation of amides with p-TsOH",

abstract = "N-Benzylamides were debenzylated efficiently with 4 equiv. of p-TsOH in refluxing toluene. Good to quantitative yields of the desired primary amides were obtained within 2-4 h from a wide variety of N-2,4-dimethoxybenzylamides. N-4-Methoxylbenzyl amides and N-benzylamides were also debenzylated cleanly. In the case of N-2,4-dimethoxylbenzylamides, selective N-debenzylation was possible in the presence of N-Fmoc, N-t-BOC or N-trityl-protection. Protected amino acid amides survived these conditions without any detectable epimerization.",

author = "Chern, \{Ching Yuh\} and Huang, \{Yu Ping\} and Kan, \{Wai Ming\}",

note = "Funding Information: We gratefully acknowledge generous support from the National Science Council of the Republic of China. ",

year = "2003",

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day = "27",

doi = "10.1016/S0040-4039(02)02738-7",

language = "English",

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journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Selective N-debenzylation of amides with p-TsOH

AU - Chern, Ching Yuh

AU - Huang, Yu Ping

AU - Kan, Wai Ming

N1 - Funding Information: We gratefully acknowledge generous support from the National Science Council of the Republic of China.

PY - 2003/1/27

Y1 - 2003/1/27

N2 - N-Benzylamides were debenzylated efficiently with 4 equiv. of p-TsOH in refluxing toluene. Good to quantitative yields of the desired primary amides were obtained within 2-4 h from a wide variety of N-2,4-dimethoxybenzylamides. N-4-Methoxylbenzyl amides and N-benzylamides were also debenzylated cleanly. In the case of N-2,4-dimethoxylbenzylamides, selective N-debenzylation was possible in the presence of N-Fmoc, N-t-BOC or N-trityl-protection. Protected amino acid amides survived these conditions without any detectable epimerization.

AB - N-Benzylamides were debenzylated efficiently with 4 equiv. of p-TsOH in refluxing toluene. Good to quantitative yields of the desired primary amides were obtained within 2-4 h from a wide variety of N-2,4-dimethoxybenzylamides. N-4-Methoxylbenzyl amides and N-benzylamides were also debenzylated cleanly. In the case of N-2,4-dimethoxylbenzylamides, selective N-debenzylation was possible in the presence of N-Fmoc, N-t-BOC or N-trityl-protection. Protected amino acid amides survived these conditions without any detectable epimerization.

UR - https://www.scopus.com/pages/publications/0037467897

UR - https://www.scopus.com/pages/publications/0037467897#tab=citedBy

U2 - 10.1016/S0040-4039(02)02738-7

DO - 10.1016/S0040-4039(02)02738-7

M3 - Article

AN - SCOPUS:0037467897

SN - 0040-4039

VL - 44

SP - 1039

EP - 1041

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 5

ER -

Selective N-debenzylation of amides with p-TsOH

Abstract

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