Ketoprofen → (R)-Ketoprofen

Participants

Reaction Conditions

Reaction Steps

(±)-2-(3-Benzoylphenyl)propionic acid (13.55 g, 53.3 mmol) was dissolved in MIBK (67.5 g) with heating. Then, (R)-(-)-3-methyl-2-phenylbutylamine (3.92 g, 24 mmol), 0.45 equivalent based on the amount of (±)-2-(3-benzoylphenyl)propionic acid, was added dropwise with stirring at 40°C. After completing the addition, the reaction solution was stirred at 40°C. for 2 hours, followed by stirring at room temperature for 6 hours and then at 10°C. for 2 hours. Then, the crystal precipitated was filtered, and the filter cake was washed with cold MIBK (25 ml) and dried to give a diastereomer salt (6.48 g) of (R)-(-)-2-(3-benzoylphenyl)propionic acid with (R)-(-)-3-methyl-2-phenylbutylamine. The yield of the product based on (R)-2-(3-benzoylphenyl)propionic acid contained in the starting material was 58.3%.

Provenance & Evidence