Chloroacetyl chloride → HCID 23122070, compound

Participants

Reaction Steps

Hexahydro-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazin-3-one (0.20 g, 0.68 mmol) was dissolved in tetrahydrofuran (3 mL). With ice cooling, diisopropylethylamine (1 mL) and chloroacetyl chloride (70 μL, 0.82 mmol) were added thereto, and the mixture was stirred at room temperature for 3 hours. Next, 4-fluoroaniline (0.13 mL, 1.4 mmol) was added thereto, and the mixture was stirred at 50° C. for 16 hours. To the reaction solution was added water, and the mixture was extracted with ethyl acetate. The organic layer 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 hexane to obtain the title compound (45 mg, yield 15%).

Provenance & Evidence