Water → tert-butyl N-(3-{[(tert-butoxycarbonyl)sulfamoyl]amino}benzyl)-N-(trifluoroacetyl)glycinate

Participants

Reaction Steps

To a solution of tert-butyl N-(3-aminobenzyl)-N-(trifluoroacetyl)glycinate (1.95 g) and triethylamine (0.981 mL) in dichloromethane (19.5 mL) was added a solution of tert-butyl (chlorosulfonyl)carbamate (1.52 g) in dichloromethane (10.0 mL) under ice-cooling, followed by stirring at room temperature for 3 hours. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated aqueous sodium chloride solution, then dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. To the residue was added ethyl acetate, and n-hexane was added thereto. The precipitated solid was collected by filtration to obtain tert-butyl N-(3-{[(tert-butoxycarbonyl)sulfamoyl]amino}benzyl)-N-(trifluoroacetyl)glycinate (2.19 g).

Provenance & Evidence