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

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.

SUBMITTER: George N

PROVIDER: S-EPMC7810210 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

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

George Nathaniel N Ofori Samuel S Parkin Sean S Awuah Samuel G SG

RSC advances 20200623 40

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 electrophi ...[more]

PMID: 33456769

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