tert-Butanol → HCID 66816414, compound

Participants

Reaction Steps

A solution of tBuOH (71.9 mg, 0.97 mmol) in dichloromethane (1.5 ml) was added to a solution of chlorosulfonyl isocyanate (137 mg, 0.97 mmol) in dichloromethane (3 ml) with stirring under ice-cooling. The mixture was stirred at 0° C. for 10 minutes and then added to a solution of 8-[(E)-2-(4-amino-2-methyl-phenyl)-ethenesulfonyl]-2-(3-trifluoromethoxy-phenyl)-1,3,8-triaza-spiro[4.5]dec-1-en-4-one (400 mg, 0.81 mmol) and triethylamine (164 mg, 1.62 mmol) in dichloromethane (3 ml). The mixture was stirred for one hour, and then quenched with water and extracted with dichloromethane. The organic layer was washed with saturated brine, and then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate-hexane) to give N-tert-butoxycarbonyl-N′-(3-methyl-4-{(E)-2-[4-oxo-2-(3-trifluoromethoxy-phenyl)-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-vinyl}-phenyl)-sulfamide (334 mg, 60%).

Provenance & Evidence