Acetic Acid → HCID 117701582, compound

Participants

Reaction Steps

To a solution of 1-benzyl 3-[3-(benzyloxy)-2-methyl-6-propanoylphenyl]azetidine-1,3-dicarboxylate (2.77 g, 5.68 mmol) obtained in Example 1-1 in dimethylformamide (16 mL), 60% sodium hydride (568 mg, 14.2 mmol) was added in small portions under cooling with ice, and then the mixture was brought back to room temperature and stirred for 1 hour. The reaction solution was cooled with ice. Then, acetic acid (1.30 mL, 22.7 mmol) was added dropwise thereto, subsequently methanol (40 mL) and concentrated hydrochloric acid (4 mL) were added thereto, and the mixture was heated with stirring at a bath temperature of 75° C. for 3 hours. The reaction solution was allowed to cool, and then methanol in the mixture was distilled off under reduced pressure. Water was added to the obtained residue, followed by extraction with ethyl acetate. The organic layer was washed with water and then dried over magnesium sulfate. The desiccant was filtered off, and then the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=80/20→50/50) to obtain 295 mg of the title compound (yield: 11%).

Provenance & Evidence