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

Nathaniel George; Samuel Ofori; Sean Parkin; Samuel G. Awuah

doi:10.1039/d0ra04110f

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

Nathaniel George
, Samuel Ofori
, Sean Parkin
, Samuel G. Awuah

Research output: Contribution to journal › Article › peer-review

26 Scopus citations

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.

Original language	English
Pages (from-to)	24017-24026
Number of pages	10
Journal	RSC Advances
Volume	10
Issue number	40
DOIs	https://doi.org/10.1039/d0ra04110f
State	Published - Jun 23 2020

Bibliographical note

Publisher Copyright:
© The Royal Society of Chemistry.

Funding

This study made use of NMR facility supported by NSF (CHE-9977388) as well as the UK X-ray facility with funds from the MRI program of the National Science Foundation (grants CHE-0319176 and CHE-1625732).

Funders	Funder number
National Science Foundation Arctic Social Science Program	CHE-0319176, CHE-9977388, CHE-1625732, 0319176

ASJC Scopus subject areas

General Chemistry
General Chemical Engineering

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10.1039/d0ra04110f

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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.",

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AU - Ofori, Samuel

AU - Parkin, Sean

AU - Awuah, Samuel G.

PY - 2020/6/23

Y1 - 2020/6/23

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AB - 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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JF - RSC Advances

IS - 40

ER -

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

Abstract

Bibliographical note

Funding

ASJC Scopus subject areas

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