Selective N-debenzylation of amides with p-TsOH

Ching Yuh Chern, Yu Ping Huang, Wai-Ming Kan

Research output: Contribution to journalArticle

35 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 languageEnglish
Pages (from-to)1039-1041
Number of pages3
JournalTetrahedron Letters
Volume44
Issue number5
DOIs
Publication statusPublished - 2003 Jan 27

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Amides
Toluene
Amino Acids

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Chern, Ching Yuh ; Huang, Yu Ping ; Kan, Wai-Ming. / Selective N-debenzylation of amides with p-TsOH. In: Tetrahedron Letters. 2003 ; Vol. 44, No. 5. pp. 1039-1041.
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Selective N-debenzylation of amides with p-TsOH. / Chern, Ching Yuh; Huang, Yu Ping; Kan, Wai-Ming.

In: Tetrahedron Letters, Vol. 44, No. 5, 27.01.2003, p. 1039-1041.

Research output: Contribution to journalArticle

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