Pyridine → HCID 86740235, compound

Participants

Reaction Steps

By the method of part E of Example 1 (N-benzyloxycarbonyl-O-benzyl-L-tyrosyl)-N2 -methyl-D-alanyl hydrazide (3.0 g.) was condensed with 3-(4-trifluoromethylphenyl)propylamine (prepared by first condensing 4-trifluoromethylbenzaldehyde with cyanoacetic acid in refluxing toluene using a catalytic amount of ammonium acetate, then decarboxylating the resulting α-cyano-β-(4-trifluoromethylpheny)acrylic acid in refluxing pyridine, and finally hydrogenating the resulting β-(4-trifluoromethylphenyl)acrylonitrile in methanolic ammonia at room temperature and 400 p.s.i.g. pressure using Raney nickel catalyst, m.r. of hydrochloride salt 189°-191°; 1.42 g.). The product was crystallized from ethanol, affording (N-benzyloxycarbonyl-O-benzyl-L-tyrosyl)-N2 -methyl-N-[3-(4-trifluoromethylphenyl)propyl]-D-alaninamide (2.85 g., m.r. 120°-122° C.).

Provenance & Evidence