A Nucleophilic Deprotection of Carbamate Mediated by 2‑Mercaptoethanol

A Nucleophilic Deprotection of Carbamate Mediated by 2‑Mercaptoethanol

Carbamates, typically used for the protection of amines, including Cbz, Alloc, and methyl carbamate, can be readily deprotected by treatment with 2-mercaptoethanol in the presence of potassium phosphate tribasic in N,N-dimethylacetamide at 75 °C. This nucleophilic deprotection protocol is superior t...

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Veröffentlicht in:Organic letters 2022-05, Vol.24 (20), p.3736-3740
Hauptverfasser: Scattolin, Thomas, Gharbaoui, Tawfik, Chen, Cheng-yi
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Sprache:eng
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Amines
Carbamates
Mercaptoethanol
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creator Scattolin, Thomas
Gharbaoui, Tawfik
Chen, Cheng-yi
description Carbamates, typically used for the protection of amines, including Cbz, Alloc, and methyl carbamate, can be readily deprotected by treatment with 2-mercaptoethanol in the presence of potassium phosphate tribasic in N,N-dimethylacetamide at 75 °C. This nucleophilic deprotection protocol is superior to the standard hydrogenolysis or Lewis acid-mediated deprotection conditions for substrates bearing a functionality sensitive to these more traditional methods.
doi_str_mv 10.1021/acs.orglett.2c01410
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subjects Amines
Carbamates
Mercaptoethanol
title A Nucleophilic Deprotection of Carbamate Mediated by 2‑Mercaptoethanol
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