4-Chlorobenzenesulfonyl chloride → HCID 10323499, compound

Participants

Reaction Steps

To a solution of 0.34 g methyl 8-amino-2,2-dimethyl-4-[3-(3-pyridyl)propyl]-octanoate in 5 ml dry methylene chloride is added a catalytic amount of 4-dimethylaminopyridine followed by 0.2 ml triethylamine and the mixture is cooled to 0°; 0.208 g (0.96 mmol) p-chlorophenylsulfonyl chloride is added, the reaction mixture is allowed to warm to room temperature and stirred for 48 h. The mixture is diluted with methylene chloride and washed with saturated sodium bicarbonate, water and brine. The organic phase is dried, filtered and evaporated to yield an amber oil which is purified by flash chromatography using 1:1 ethyl acetate/hexane to yield methyl 8-(p-chlorophenylsulfonamido)-2,2-dimethyl-4-[3-(3-pyridyl)propyl]-octanoate; IR (CH2Cl2): 3381, 1729, 1164 cm-1 ; NMR (CDCl3): delta 3.57 (s,3H), 2.9 (q,2H), 2.53 (t,2H), 1.12 (s,6H).

Provenance & Evidence