4-Chlorobenzenesulfonyl chloride → Ethyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)propyl]-octanoate

Participants

Reaction Steps

To a solution of 2200 g of crude ethyl 8-amino-4-[3-(3-pyridyl)-propyl]-octanoate in 28.8 L of dichloromethane is added 1377 g of triethylamine. The solution is cooled to 0° and a solution of 1435 g of p-chlorophenylsulfonyl chloride in 14.3 L of dichloromethane is added over a period of 45 minutes maintaining the temperature below 5°. The reaction is allowed to slowly warm up to room temperature overnight. The reaction mixture is washed 3 times with 15 L of sodium bicarbonate and then with water, dried over sodium sulfate and evaporated to dryness to yield ethyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)-propyl]-octanoate as an oil.

Provenance & Evidence