Chloroform → HCID 69837520, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1.6 g of methyl (3R,4R)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-3-acetate dihydrochloride in 30 cm3 of dioxane, to which had been added 2.6 cm3 of 5N aqueous sodium hydroxide solution, was stirred for 6 hours at a temperature in the region of 65° C. After concentrating the reaction mixture under reduced pressure (5 kPa) at a temperature in the region of 40° C., a residue was obtained, which residue was taken up in 2 times 30 cm3 of chloroform and which was concentrated as under the above conditions. The residue was purified by chromatography at atmospheric pressure on a column of silica gel (particle size 20-45 μm; diameter 3 cm; silica volume 100 cm3), elution was carried out with a chloroform/methanol/28% aqueous ammonia (12/3/0.5 by volume) mixture, and 30-cm3 fractions were collected. The fractions comprising the expected product were combined and concentrated as above. 1.5 g of a colorless lacquer were obtained, which product was taken up in 20 cm3 of diethyl ether, filtered, and washed with 2 times 10 cm3 of diethyl ether. The product was dried under partial pressure (5 kPa) and then to constant weight in an oven under reduced pressure (10 Pa) at a temperature in the region of 40° C. 1.35 g of (3R,4R)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-3-acetic acid were obtained in the form of a white solid.

Provenance & Evidence