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KMID : 0043319920150020142
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Archives of Pharmacal Research
1992 Volume.15 No. 2 p.142 ~ p.145
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Synthesis of Hexaprofen [2-(4-Cyclohexylphenyl) propionic Acid]
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Choi HD
Ma JJ/Son BW
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Abstract
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A novel preparative method for hexaprofen, which is a potent antiinflammatory agent, is described. Friedel-Crafts reaction of cyclohexylbenzene with ethyl alpha-chloro-alpha-(methylthio) acetate 1 and alpha-chloro-alpha-(methylthio) acetonitrile 2 afforded ethyl 2-(methylthio)-2-(4-cyclohexylphenyl) acetate 7 and 2-methylthio-2-(4-cyclohexylphenyl) acetonitrile 8, respectively. Compounds 7 and 8 were converted into the corresponding ethyl 2-methylthio-2-(4-cyclohexylphenyl) propionate 9 and 2-methylthio-2-(4-cyclohexylphenyl) propionitrile 10 by methylation with sodium hydride and methyl iodide. Hexaprofen 13 was prepared by hydrolysis of ethyl 2-(4-cyclohexylphenyl) propionate 11 and of 2-(4-cyclohexylphenyl) propionitrile 12 followed by desulfurization of compounds 9 and 10.
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