Acetic Acid → Methyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)-propyl]-octanoate

Participants

Reaction Steps

A solution of 130.15 g of sodium methoxide in 2.4 L methanol is added at room temperature to a solution of 5469 g of ethyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)-propyl]-octanoate in 52.3 L of methanol. The mixture is stirred for 40 hours under nitrogen. Glacial acetic acid (145.5 g) is added and the reaction mixture is evaporated to dryness at 60° and 3 mm Hg. The residue is dissolved in 40 L of ethyl acetate, the solution is washed with dilute sodium bicarbonate solution and then with 5% sodium bisulfite, dried over sodium sulfate, treated with charcoal and evaporated to dryness to yield crude methyl 8-(p-chloro-phenylsulfonamido)-4-[3-(3-pyridyl)-propyl]-octanoate.

Provenance & Evidence