Synthesis and characterization of peptidomimetics containing oxazolidin-2-one and oxazolidine scaffolds

Abstract

In this paper, we report the synthesis of peptidomimetics containing oxazolidin-2-one and oxazolidine rings. The two of these heterocyclic peptidomimetics novel series were obtained from serine as starting material through an efficient intramolecular cyclization. In the case of oxazolidine, the formation of only one diastereoisomer was observed.

Protecting-Group-Free Mechanosynthesis of Amides from Hydroxycarboxylic Acids: Application to the Synthesis of Imatinib

“…Dipeptide 16 was obtained as a single diastereomer (>99% dr), indicating that no epimerization occurred during the reaction. The synthesis of peptides 14 and 16 was previously performed in dichloromethane or dimethylformamide solutions, using carbodiimides (EDC or DCC) as coupling reagents and 1-hydroxybenzotriazole (HOBt) as an additive 75,76. The reaction was much slower (over 16 h) in comparison with the essentially solvent-free and rapid (1 h) mechanochemical protocol.…”