Tert-Butyloxycarbonyl-protected amino acid ionic liquids and their application to dipeptide synthesis.

Abstract

Care should be taken when using amino acid ionic liquids (AAILs) for organic synthesis because of their multiple reactive groups. To expand the applicability of AAILs, we prepared a series of room-temperature ionic liquids derived from commercially available tert-butyloxycarbonyl-protected amino acids (Boc-AAILs). The resulting protected AAILs were used as the starting materials in dipeptide synthesis with commonly used coupling reagents. The distinctive coupling reagent N,N′-diethylene-N′′-2-chloroethyl thiophosphoramide was found to enhance amide formation in the Boc-AAILs without addition of base, giving the dipeptides in satisfactory yields in 15 min.