Ketoprofen → Dexketoprofen

関与物質

反応手順

(±)-2-(3-Benzoylphenyl)propionic acid (51 g, 0.2 mol) was dissolved in MIBK (290 ml) and (S)-(+)-3-methyl-2-phenylbutylamine (19.6 g, 0.12 mol) was added dropwise with stirring. After completing the addition, the reaction solution was maintained at 35° C. to 40° C. for one hour and stirred at room temperature for 5 hours and then at 10° C. for 3 hours. Then, the crystal precipitated was filtered and the filter cake was washed with cold MIBK (70 ml) to give a wet cake (67 g). To this wet cake was added MIBK (240 ml) and the mixture was heated to dissolve at 77° C. Then, the mixture was cooled and stirred at 10° C. for 2 hours. Then, the crystal precipitated was filtered to give a diastereomer salt (30.2 g) of (S)-(+)-2-(3-benzoylphenyl)propionic acid with (S)-(+)-3-methyl-2-phenylbutylamine. This diastereomer salt was treated with hydrochloric acid to give (S)-(+)-2-(3-benzoylphenyl)propionic acid (18.26 g). The optical purity of this propionic acid was 99.2% e.e. The yield of the product based on (S)-(+)-2-(3-benzoylphenyl)propionic acid contained in the starting material was 71.6% e.e.

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