Water → HCID 86724968, compound

Participants

Reaction Steps

p-Toluenesulfonyl chloride (611 mg, 3.20 mmol) was added at room temperature to a solution of 6-[(4S)-4-(hydroxymethyl)-2-oxopyrrolidin-1-yl]-2H-1,4-benzoxazin-3(4H)-one (420 mg, 1.60 mmol) in pyridine (5 ml) and the mixture was stirred for 24 hours. The reaction solution was concentrated under reduced pressure and the obtained resultant was dissolved in dichloromethane and washed with 1N hydrochloric acid. The aqueous layer was extracted with dichloromethane and the organic layer was washed sequentially with water and a saturated sodium hydrogen carbonate aqueous solution. The organic layer was dried over anhydrous sodium sulfate, the drying agent was removed by filtration and the filtrate was concentrated under reduced pressure. The obtained brown solid was dissolved in N,N-dimethylformamide (5 mL), sodium azide (208 mg, 3.20 mmol) was added thereto and the mixture was stirred at 80° C. for 2 hours. After adding water, the reaction solution was poured into a mixture of dichloromethane and a saturated sodium hydrogen carbonate aqueous solution and extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, the drying agent was removed by filtration and the filtrate was concentrated under reduced pressure. Dichloromethane was added to the obtained residue to prepare a slurry and the solid was collected by filtration to yield 300 mg of the title compound in the form of a light yellow solid. The residue obtained by concentrating the filtrate was purified by silica gel column chromatography (dichloromethane/methanol) to yield 132 mg of the title compound in the form of a light yellow solid. Total yield 432 mg (94%).

Provenance & Evidence