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 |
All Science Journal Classification (ASJC) codes
- Biochemistry
- Drug Discovery
- Organic Chemistry
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Cite this
Chern, C. Y., Huang, Y. P., & Kan, W. M. (2003). Selective N-debenzylation of amides with p-TsOH. Tetrahedron Letters, 44(5), 1039-1041. https://doi.org/10.1016/S0040-4039(02)02738-7