Selective N-debenzylation of amides with p-TsOH |
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| Authors: | Ching-Yuh ChernYu-Ping Huang Wai Ming Kan |
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| Institution: | a Department of Applied Chemistry, Chao Yang University of Technology, Taichung, Taiwan 413, ROC
b Department of Pharmacology, National Cheng Kung University, Tainan, Taiwan 701, ROC |
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| 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. |
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| Keywords: | N-debenzylation N-2 4-dimethoxybenzylamide p-TsOH |
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