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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1459044Generated: October 26, 2026

Ketoprofen → Dexketoprofen

https://huagongshe.com/reaction/1459044

Reaction equation

Participants

RoleNameHCIDCharge
ReactantKetoprofenHCID 3825—
Reactant(S)-3-Methyl-2-phenylbutylamineHCID 10176271—
SolventMethyl Isobutyl KetoneHCID 7909—
ProductDexketoprofenHCID 66755065.6%

Reaction Steps

That is, (±)-2-(3-benzoylphenyl)propionic acid (12.7 g, 50 mmol) was dissolved in MIBK (76 ml) and (S)-(+)-3-methyl-2-phenylbutylamine (4.9 g, 30 mmol) was added dropwise at 40° C. This reaction solution was stirred at 35° C. to 40° C. for one hour, followed by at room temperature for 5 hours and then at 10° C. to 15° C. for one hour. Then, the crystal precipitated was filtered, and the filter cake was washed with cold MIBK (30 ml) and dried to give a diastereomer salt (8.34 g) of (S)-(+)-2-(3-benzoylphenyl)propionic acid with (S)-(+)-3-methyl-2-phenylbutylamine. The yield of the product based on (S)-(+)-2-(3-benzoylphenyl)propionic acid contained in the starting material was 80%. Melting point: 129°-131° C. Optical purity: 94.3% e.e.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05852209
Source datasetuspto-grants-1998_12
ORD IDord-1217c5459dd7497f9a525c87efd59867
Source noteuspto-grants-1998_12