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Simple and efficient cleavage of the N-(1-phenylethyl) unit of carboxamides with methanesulfonic acid
Authors:Seunguk Paik  Jun Young Lee
Institution:Department of Chemical System Engineering, Keimyung University, Taegu 704-701, Republic of Korea
Abstract:Cleavage of the N-(1-phenylethyl) unit of carboxamides using less than 1 equiv of MsOH in refluxing toluene was found to be simple and very efficient leading to the desired amides in good to excellent yields, and also proved to be more effective compared with reductive methods using hydrogen sources, or acid hydrolysis reagents such as TFA and TsOH. The method selectively cleaved only the N-(1-phenylethyl) group of N-benzyl-N-(1-phenylethyl)amides.
Keywords:N-(1-Phenylethyl)carboxamides  Methanesulfonic acid  Deprotection
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