Efficient preparation of aminoxyacyl amides, aminoxy hybrid peptides, and alpha-aminoxy peptides.

Research paper by Alan R AR Katritzky, Ilker I Avan, Srinivasa R SR Tala

Indexed on: 17 Oct '09Published on: 17 Oct '09Published in: Journal of Organic Chemistry


N-(Pg-alpha-aminoxy acids) 1a-g are converted to N-(Pg-alpha-aminoxyacyl)benzotriazoles 2a-g, which react under mild conditions with amines, alpha-amino acids/alpha-dipeptides, and alpha-aminoxy acids to give aminoxyacyl amides 3a-g, (3e+3e'), and (3g+3g'), aminoxy hybrid peptides 4a-h, (4a+4a'), 6a-d, 9a-e, (9a+9a'), and (9b+9b'), and alpha-aminoxy peptides 10a,b in good yields without racemization.