Mild deprotection of the <i>N-tert</i>-butyloxycarbonyl (<i>N</i>-Boc) group using oxalyl chloride
Nathaniel George, Samuel Ofori, Sean Parkin, Samuel G. Awuah
Abstract
-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.
Topics & Concepts
Oxalyl chlorideGroup (periodic table)ChlorideChemistryMedicinal chemistryCombinatorial chemistryOrganic chemistrySynthesis and pharmacology of benzodiazepine derivativesFluorine in Organic ChemistryAsymmetric Synthesis and Catalysis