Synthesis of N(α), N(β)-alkylated diaminopropionic acid analogs

Article abstract of DOI:10.1016/0040-4039(95)00968-i

A general route for the preparation of N(α)-alkylated and N(β)- alkylated derivatives of diaminopropionic acids is described. Nucleophilic ring opening of N-tosyl aziridine-2-t-butyl carboxylate with primary amines leads to the corresponding N(β)-alkyl derivative. Reaction of the N(α)- tosyl diaminopropionic derivative with Cs₂CO₃ and alkyl iodide selectively produces the N(α)-alkylated compound.