Benzoic Acid → HCID 54357787, compound

Participants

Reaction Steps

To a solution of 8-chloro-11-[(6S,8S)-8-hydroxy-1,4-diazabicyclo[4.3.0]non-4-yl]-dibenz[b,f]-1,4-oxazepine (64 mg, 0.173 mmol), benzoic acid (42.3 mg, 0.346 mmol) and triphenylphosphine (91.0 mg, 0.346 mmol) in anhydrous methylene chloride (20 mL) at 0° C. under argon was added diethyl azodicarboxylate (60.3 mg, 0.346 mmol) via syringe. The reaction mixture was allowed to warm to room temperature and was stirred overnight. The product was absorbed onto silica gel and purified by flash column chromatography using 10% acetone in hexanes as the eluent to give 51.6 mg (63%) of 8-chloro-11-[(6S,8R)-8-benzoyl-1,4-diazabicyclo[4.3.0]non-4-yl]-dibenz[b,f]-1,4-oxazepine as an off-white solid; mp (succinic acid salt) 92°-94° C.; Rf(25% acetone/hexanes): 0.45; HRMS (FAB): MH+ of C27H24N3O3Cl, calculated 474.1584, found 474.1595.

Provenance & Evidence