Oxalyl chloride → HCID 23121945, compound

Participants

Reaction Steps

To a solution of 4-fluorocinnamic acid (50 mg, 0.30 mmol) in tetrahydrofuran (1 mL) were sequentially added oxalyl chloride (46 mg, 0.36 mmol) and N,N-dimethylformamide (one drop), and the mixture was stirred at room temperature for 1 hour. The reaction solution was concentrated under reduced pressure. A solution of hexahydro-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazin-3-one (60 mg, 0.20 mmol) in tetrahydrofuran (1.5 mL) and diisopropylethylamine (0.3 mL) were sequentially added thereto, and the mixture was stirred at room temperature for 3 hours. To the reaction solution was added an aqueous saturated sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:1) and crystallized from ethyl acetate-diisopropyl ether to obtain the title compound (32 mg, yield 36%).

Provenance & Evidence