Gallou, Fabrice (2024) Protecting-Group-Free Mechanosynthesis of Amides from Hydroxycarboxylic Acids. RSC Mechanochemistry, 1. pp. 189-195.

Abstract

Mechanochemical methods for assembling carbon-nitrogen bonds play a central role in the ongoing green chemistry-driven renovation of organic synthesis.However, there is a paucity of reports addressing chemoselective issues in these transformations, such as the tolerance of unmasked hydroxyl groups. Screening of various amide coupling conditions revealed 1 ethyl 3 (3 dimethylaminopropyl)carbodiimide (EDC) in combination with ethyl acetate as a liquid-assisted grinding (LAG) solvent as the most selective amide coupler, delivering 76–94% yields of the respective amide products from unprotected hydroxycarboxylic acids. Boc-protected tyrosine and serine with unmasked OH functionalities were successfully involved in peptide couplings.

Item Type:	Article
Date Deposited:	04 Jun 2024 00:46
Last Modified:	04 Jun 2024 00:46
URI:	https://oak.novartis.com/id/eprint/51656