Acetic Anhydride → HCID 20562575, compound

Participants

Reaction Steps

A mixture of 4-cyclopropanecarbonyl-9-amino-3,4,5,6-tetrahydro-2H-1,5-methano-1,4-benzodiazocine (8 g.) and acetic anhydride (50 ml.) was heated on a steam bath for two hours. Pyridine was added and heating was continued for three hours. The mixture was concentrated to dryness. The residue was partitioned between aqueous base and chloroform. The chloroform layer was dried and concentrated to dryness. Recrystallization of the residue from acetonitrile afforded a product (m.r. 117°-187° C.), which to remove product of diacetylation was warmed with dilute aqueous sodium bicarbonate. Extraction of the resulting mixture with chloroform and concentration of the chloroform extract to dryness afforded 4-cyclopropanecarbonyl-9-acetamido-3,4,5,6-tetrahydro-2H-1,5-methano-1,4-benzodiazocine (about 8 g.), the compound of Formula VI wherein Q' is cyclopropanecarbonyl and R"CONH is acetamido.

Provenance & Evidence