tert-Butanol → HCID 86614314, compound

Participants

Reaction Steps

To a solution of chlorosulfonyl isocyanate (1.5 eq) in anhydrous 1,2-dichloroethane (0.1-0.5 M) at 0° C. was added 1.5 eq of tert-butanol as a solution in anhydrous 1,2-dichloroethane (0.5 M). The mixture was allowed to warm to room temperature while stirring and was then cooled to 0° C. again. A suspension of aniline-ester from general procedure E (1.0 eq) in 1,2-dichloroethane (0.3-0.5 M) and 2.5 eq DIEA was cooled to 0° C. and the chlorosulfonyl isocyanate-tert-butanol mixture was added drop-wise while stirring. The mixture was stirred at room temperature for 1 hour, then diluted with water/CH2Cl2 and the layers separated. The organic layers were combined and washed with water and brine. The organic phase was then dried over Na2SO4, filtered, and the filtrate was concentrated and purified by silica gel chromatography to afford the aniline N-Boc sulfamide derivative.

Provenance & Evidence