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 | |
| Publication status | Published - 2003 Jan 27 |
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All Science Journal Classification (ASJC) codes
- Biochemistry
- Drug Discovery
- Organic Chemistry
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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 journal › Article
TY - JOUR
T1 - Selective N-debenzylation of amides with p-TsOH
AU - Chern, Ching Yuh
AU - Huang, Yu Ping
AU - Kan, Wai-Ming
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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U2 - 10.1016/S0040-4039(02)02738-7
DO - 10.1016/S0040-4039(02)02738-7
M3 - Article
VL - 44
SP - 1039
EP - 1041
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 5
ER -