Dichloromethane → tert-Butyl(3aS,6S,7aR)-6-(dimethylcarbamoyl)-2,2-dioxohexahydro-2,1,3-benzothiadiazole-1(3H)-carboxylate

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Reaction Conditions

Reaction Steps

Methylene chloride (200 ml) and triethylamine (18.5 ml) were added to tert-butyl {[(1R,2R,5S)-5-(dimethylcarbamoyl)-2-hydroxycyclohexyl]sulfamoyl}carbamate (20 g), and the obtained solution was then cooled to approximately 0° C. Methanesulfonyl chloride (5.2 ml) was added dropwise to the reaction solution, and the obtained mixture was then stirred for approximately 1 hour. Thereafter, water (100 ml) was added to the reaction mixture, and the organic layer was then separated. The solvent was distilled off from the organic layer under reduced pressure. To the residue, acetonitrile (200 ml) and triethylamine (15.4 ml) were added, and the obtained mixture was then heated to approximately 90° C., followed by stirring the mixture for approximately 2 hours. Thereafter, the reaction mixture was cooled to room temperature, 10% saline (100 ml) was then added to the mixture, and the organic layer was then separated. The aqueous layer was extracted with ethyl acetate (100 ml) again. The gathered organic layers were concentrated, and the obtained residue was purified by silica gel column chromatography to obtain the title compound (14.02 g, yield: 74%) in the form of powder.

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