Mild Deprotection of the N-Tert-Butyloxycarbonyl (N-Boc) Group Using Oxalyl Chloride

Authors

Nathaniel George, University of KentuckyFollow
Samuel Ofori, University of KentuckyFollow
Sean R. Parkin, University of KentuckyFollow
Samuel G. Awuah, University of KentuckyFollow

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.

Document Type

Article

Publication Date

2020

Notes/Citation Information

Published in RSC Advances, v. 10, issue 40.

© The Royal Society of Chemistry 2020

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.

Digital Object Identifier (DOI)

https://doi.org/10.1039/D0RA04110F

Funding Information

The authors acknowledge support of the Center for Pharmaceutical Research and Innovation (NIH P20 GM130456).

Related Content

Electronic supplementary information (ESI) available. CCDC 1998517. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/d0ra04110f.

The crystallographic data and the correction for this article are available for download as additional files listed at the end of this record.

Repository Citation

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.
https://uknowledge.uky.edu/chemistry_facpub/174