Sodium Hydroxide → (3r,4r)-1-[2-(Thien-2-ylthio)ethyl]-4-[3-(r,s)-amino-3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-carboxylic acid

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Reaction Steps

1 cm3 of 5N aqueous sodium hydroxide solution is added with stirring, at a temperature in the region of 20° C., to a solution of 0.05 g of methyl (3R,4R)-1-[2-(thien-2-ylthio)ethyl]-4-[3-(R,S)-amino-3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-carboxylate in 2 cm3 of dioxane and 2 cm3 of methanol, and then the combined mixture is brought to reflux and refluxed for 20 hours. The mixture is concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. The residue obtained is dissolved in 6 cm3 of distilled water The aqueous phase is washed with 2 cm3 of methylene chloride and then evaporated to dryness. The residue is taken up in 2 cm3 of isopropanol and the insoluble material is washed with 2 cm3 of isopropanol and then dried to give 0.05 g of (3R,4R)-1-[2-(thien-2-ylthio)ethyl]-4-[3-(R,S)-amino-3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-carboxylic acid, sodium salt.

Provenance & Evidence