Sodium Hydroxide → HCID 69353164, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 0.73 g of methyl. (3R,4R)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-3-yl)prop-2-ynyl]piperidine-3-carboxylate, 7.6 cm3 of dioxane, and 1.22 cm3 of 5N aqueous sodium hydroxide solution was heated at a temperature in the region of 60° C. with stirring for 3 hours 30 minutes. After cooling to a temperature in the region of 20° C., the reaction mixture was concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. The residue obtained was purified by chromatography under argon pressure (55 kPa) on a column of silica gel (particle size 40-63 μm; diameter 5 cm; silica volume 120 cm3), elution was carried out first with 1120 cm3 of a dichloromethane/methanol/acetonitrile (92/8/7 by volume) mixture. Elution was subsequently carried out with 224 cm3 of the same mixture (but with a composition of 92/12/7 by volume), then 224 cm3 of the same mixture (with a composition of 92/16/7 by volume), then 400 cm3 of a dichloromethanel methanol (50/50 by volume) mixture, and finally 400 cm3 of pure methanol. A fraction of 112 cm3 was collected, followed by 7-cm3 fractions. Fractions 173 to 468 were combined and then evaporated under reduced pressure (2 kPa) at a temperature in the region of 35° C. A foam was obtained, which foam was dried under reduced pressure (30 Pa) at a temperature in the region of 30° C. for 4 to 5 hours. 0.33 g of (3R,4R)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-3-yl)prop-2-ynyl]piperidine-3-carboxylic acid was obtained in the form of a beige-colored solid with a foamy appearance melting at 113-115° C.

Provenance & Evidence