Aqueous MW eco-friendly protocol for amino group protection

NARDI, MONICA; HERRERA CANO, NATIVIDAD; COSTANZO, PAOLA; OLIVERIO, MANUELA

Congreso; 3rdInternational Symposium on Green Chemistry (ISGC-2015); 2015

In this work is presented a new catalyst-free and on-water method for protection of amines and amino acids with di-tert-butyl dicarbonate, 9-fluorenylmethoxycarbonyl chloride, acetyl chloride and tosyl chloride. The protection can be realized in a few minutes under microwave-assistance. The reaction proved to be chemoselective in presence of ambident nucleophiles and water solution of di- tert-butyl carboxylic acid or chloride acid are the only wastes produced. Synthetic organic protocols using greener and more efficient methodologies are crucial for the development of more sustainable processes. This article highlights the importance of water in organic synthesis and exhibits a novel and efficient route for water-mediated N-protection of amines with MW. The absence of acid/base and the use of water makes present procedure environmentally friendly. In the light of these premises, further developments of benign by design methodologies are expected in the coming study. The authors believe that these methods of sustainable protection are stimulus to the development of synthetic methods for peptides that meet the 12 principles of Green Chemistry