2-Butenoic acid, 4-oxo-4-phenyl-, ethyl ester → [2-Oxo-3-(2-oxo-5-phenyl-tetrahydro-furan-3-ylamino)-2,3,4,5-tetrahydro-benzo[b]azepin-1-yl]-acetic acid tert-butyl ester

Participants

Reaction Steps

Ethyl 3-benzoylacrylate (13a) (55.6 g, 250 mmoles) is dropped into a solution of (3S)-3-amino-1-t-butoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-benzazepin-2-one (11) (66.2 g, 227 mmoles) in 200 ml of toluene, at room temperature in 1 h. The resulting mixture is left under stirring for 18 h, then added with 10% Pd—C (26 g, 22 mmoles) and hydrogenated at 3 atm for 18 h at room temperature. After completion of the reaction, the catalyst is filtered off, 50 ml of acetic acid are added and volatiles are distilled off at 110–120° C. inner temperature.

Provenance & Evidence