3-Chloropropanesulphonyl chloride → 3-(3-Chloropropylsulfonylamino)-2-methoxy-1-octadecylcarbamoyloxypropane

Participants

Reaction Steps

To a solution of 3.368 g (10.22 mM) of 3-hexadecyloxy-2-methoxypropylamine IV a3 in 35 ml of dichloromethane and 1.85 ml (13.29 mM) of triethylamine is added 1.99 g (11.24 mM) of 3-chloropropanesulfonyl chloride with ice-cooling and the mixture is stirred at room temperature for 4 hours and then heated for 30 minutes with stirring. After the solvent is evaporated, the residue is purified by the column chromatography on silica gel with a n-hexane-ethyl acetate (3:1) mixture as an eluent. The product is recrystallized form methanol to give 4.15 g (8.827 mM) of 3-(3-chloropropylsulfonylamino)-1-hexadecyloxy-2-methoxypropane III a3 as a colorless powder in 86% yield.

Provenance & Evidence