A novel 2H-azirin-3-amine as a synthon for a sulfur containing dipeptide segment

Starting with tetrahydro-2H-thiopyran-4-carboxylic acid and methyl prolinate, the novel 2H-azirin-3-amine (S)-N-(1-aza-6-thiaspiro[2.5]oct-1-en-2-yl)proline methyl ester was synthesized. In reactions with benzoic acid, thiobenzoic acid and Boc-valine, respectively, its usefulness as a synthon for the dipeptide (S)-N-[(4-aminotetrahydro-2H-thiopyran-4-yl)carbonyl]proline in peptide synthesis was demonstrated