One molar equivalent of methanesulfonic acid in hexafluoroisopropanol affords facile deprotection of N-Cbz groups at room temperature, often in quantitative yields. The method is an operationally simple alternative to the traditional standby of catalytic hydrogenation and enables N-Cbz removal in the presence of hydrogenation-labile functionality without reliance on harsher conditions such as HBr in acetic acid. An effective new TLC stain based on the method is also presented for use with otherwise difficult to visualize carbamates.

Facile N-Cbz cleavage by stoichiometric sulfonic acid in HFIP

ACS Spring 2022

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