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

Producción científica: Article › revisión exhaustiva

28 Citas (Scopus)

Resumen

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.

Idioma original	English
Páginas (desde-hasta)	24017-24026
Número de páginas	10
Publicación	RSC Advances
Volumen	10
N.º	40
DOI	https://doi.org/10.1039/d0ra04110f
Estado	Published - jun 23 2020

Nota bibliográfica

Publisher Copyright:
© The Royal Society of Chemistry.

Financiación

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).

Financiadores	Número del financiador
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 - Parkin, Sean

AU - Awuah, Samuel G.

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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

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

Resumen

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Financiación

ASJC Scopus subject areas

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