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

39 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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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. ",

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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.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

Selective N-debenzylation of amides with p-TsOH

Abstract

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