Rapid and convenient semi-automated microwave assisted solid-phase synthesis of arylopeptoids.

Jakob Ewald Rasmussen (1) , Marcello Massimo Boccia (1) , John Nielsen (2) , Claude Taillefumier (3) , Sophie Faure (3) , Thomas Hjelmgaard (1)

1 Department of Chemistry [Copenhagen]
2 University of Copenhage, Faculty of Health and Medical Sciences
3 ICCF - Institut de Chimie de Clermont-Ferrand

A facile and expedient route to the synthesis of arylopeptoid oligomers (N-alkylated aminomethyl benz-amides) using semi-automated microwave-assisted solid-phase synthesis is presented. The synthesis was optimized for the incorporation of side chains derived from sterically hindered or unreactive amines and both ortho- and para-substituted arylo-backbones. By utilizing this optimized protocol a complex nonameric arylopeptoid was synthesized in less than 11 h, featuring a novel alternating ortho-, meta-, and para-substituted backbone pattern and a variety of chemically diverse and challenging side chains.

Mots clés: Aromatic oligoamides; Solid-phase synthesis; Automated synthesis; Microwave-assisted synthesis; Submonomer synthesis

Domaines: Chimie

Jakob Ewald Rasmussen, Marcello Massimo Boccia, John Nielsen, Claude Taillefumier, Sophie Faure, et al.. Rapid and convenient semi-automated microwave assisted solid-phase synthesis of arylopeptoids.. Tetrahedron Letters, 2014, 55, pp.5940-5943. ⟨10.1016/j.tetlet.2014.08.119⟩. ⟨hal-01077433⟩