Chlorosulfamic acid → 6-(3,5-Diisopropyl-4-sulfamoyloxy-phenyl)-hexanoic acid ethyl ester

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Reaction Steps

Sodium hydride (0.257 g, 6.4 mmol) was added to 6-(4-hydroxy-3,5-diisopropyl-phenyl)-hexanoic acid ethyl ester (1.46 g, 5.0 mmol) in dimethylformamide (20 mL) at 0° C. over about 3 minutes. The cooling bath was removed, and the mixture was stirred at room temperature for 10 minutes. The reaction mixture was cooled to zero degrees and sulfamoyl chloride (1.18 g, 10.3 mmol) was added over ~ 3 minutes. The reaction mixture was stirred 1.5 hours at zero degrees and was quenched by adding saturated aqueous sodium bicarbonate solution. The mixture is diluted with diethyl ether (300 mL) and water (100 mL). The organic layer is washed with water (3×100 mL), brine, dried over magnesium sulfate, filtered, and concentrated to an oil. The oil is chromatographed on silica gel using 4:1 hexanes/ethyl acetate as eluant. The title compound is obtained as a light yellow oil, 1.29 g. CI Mass Spectrum: [M+H+ ]+ =400.

Provenance & Evidence