Ethyl chloroformate → N-(3,5-Bistrifluoromethyl-benzyl)-N-(8-chloro-1-(5-ethoxy-[1,3,4]oxadiazol-2-yl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-acetamide

Participants

Reaction Steps

To a stirring solution of N-(3,5-Bistrifluoromethyl-benzyl)-N-(8-chloro-1-hydrazinocarbonyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-acetamide (0.13 mmol, 73 mg) in MeOH (1 mL) was added ethyl chloroformate (0.41 mmol, 45.0 μL) and the reaction mixture was refluxed for 12 h. After completion (by TLC), the mixture was cooled, diluted with EtOAc (20 mL), washed with water and brine. The organic layer was dried over Na2SO4 and concentrated in vacuo to afford the crude product as viscous oil. Purification by flash silica gel column chromatography gave the title compound as colorless foam; Rf 0.40 (EtOAc/Hexane, 1:1, v/v); MS (ES+): 599 (M+Na+).

Provenance & Evidence