Chiral Separation of Ibuprofen

  • Author: ChemViews
  • Published Date: 16 February 2011
  • Source / Publisher: Chemistry An Asian Journal/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
thumbnail image: Chiral Separation of Ibuprofen

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The pharmacological activity of ibuprofen, a common painkiller and anti-inflammatory drug, arises predominantly from its (S)-form. Separation of the (R)- and (S)-forms is difficult as they differ only in optical polarity.

The continuous and simultaneous reaction/separation of ibuprofen racemate has been reported by Dong-Pyo Kim and co-workers, Chungnam National University, South Korea. They use an inorganic polymer-chip device with triple-laminar flow. A feed phase with Candida rugosa lipase was used to facilitate esterification of (S)-ibuprofen due to its selective chiral recoginition and resolution. The (S)-ibuprofen ester was then transported through an ionic liquid which acted as a pseudo-membrane. Finally, conversion into (S)-ibuprofen was achieved by H2SO4 acid hydrolysis in a receiving stream.

The separated ibuprofen revealed very high chiral purity, with 99.9 % enantiomeric excess throughout the process conditions.

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Magazine of Chemistry Europe (16 European Chemical Societies) published by Wiley-VCH