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.
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The authors acknowledge support of the Center for Pharmaceutical Research and Innovation (NIH P20 GM130456).
The crystallographic data and the correction for this article are available for download as additional files listed at the end of this record.
George, Nathaniel; Ofori, Samuel; Parkin, Sean R.; and Awuah, Samuel G., "Mild Deprotection of the N-Tert-Butyloxycarbonyl (N-Boc) Group Using Oxalyl Chloride" (2020). Chemistry Faculty Publications. 174.