Mild deprotection of the N- tert-butyloxycarbonyl (N-Boc) group using oxalyl chloride

RSC Adv. 2020;10(40):24017-24026. doi: 10.1039/D0RA04110F. Epub 2020 Jun 23.

Abstract

We report a mild method for the selective deprotection of the N-Boc group from a structurally diverse set of compounds, encompassing aliphatic, aromatic, and heterocyclic substrates by using oxalyl chloride in methanol. The reactions take place under room temperature conditions for 1-4 h with yields up to 90%. This mild procedure was applied to a hybrid, medicinally active compound FC1, which is a novel dual inhibitor of IDO1 and DNA Pol gamma. A broader mechanism involving the electrophilic character of oxalyl chloride is postulated for this deprotection strategy.