Profen resolution

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C - Chemistry, Metallurgy

07

C

C07C 53/132 (2006.01) C07B 57/00 (2006.01) C07C 51/487 (2006.01)

Patent

CA 2128525

2128525 9314056 PCTABS00024 A process is disclosed that is useful for separating the enantiomers of a racemic mixture of an aliphatic carboxylic acid having formula (I), where R1 is hydrogen or alkyl, R2, R3 and R4 are independently different and are hydrogen, alkyl, cycloalkyl, alkenyl, alkynyl, phenyl, substituted phenyl, naphthyl, substituted naphthyl, heteroaryl, substituted heteroaryl, haloalkyl, alkoxyalkyl, alkylthioalkyl, phenylalkyl, substituted phenylalkyl, heteroalkylalkyl, substituted heteroalkylalkyl or cycloalkylalkyl. The process comprises forming a conglomerate salt by reacting the racemic mixture with a base, the conglomerate salt being a mixture of the enantiomeric salts and having the following properties: i) the infrared spectrum of each of the enantiomeric salts, individually, and of the racemate salt are superposable; ii) the melting point of each of the enantiomeric salts, individually, is greater than the melting point of the racemate salt; and iii) the solubility of each of the enantiomeric salts, individually, is less than the solubility of the racemate salt in the same solvent. The enantiomeric salts are readily separable from the racemic mixture.

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