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Sunday, 29 July 2012

Enantiomeric Ibuprofen via Environmentally Benign Selective Crystallization

 Ibuprofen was developed by the Boots Group, a pharmacy chain in the United Kingdom, in the 1950’s-1960s. It was discovered by Stewart Adams (along with John Nicholson, Andrew RM Dunlop, Jeffrey Bruce Wilson & Colin Burrows). The Boots group originally licensed Ibuprofen to two large drug companies. The first was Whitehall Laboratories (who sold the product as Advil) and the second was Upjohn who used Bristol-Meyers to market their product “Nuprin”. Boots held the patent until 1985 along with the rights to market it until 1986. Afterwards new products entered the market creating multiple new “generic” brands.

Selective crystallization of ibuprofen/lysinate from 1 mol of (R,S)-(racemic) ibuprofen and ≤0.5 mol of (S)-lysine in aqueous ethanol affords either (S)-(+)-ibuprofen/(S)-lysinate or (R)-ibuprofen/(S)-lysinate (in preponderance) depending on the crystallization conditions. The previously unreported temperature selective diastereo-recognition (TSD) provides simple and efficient means to prepare either enantiomer of ibuprofen from (R,S)-ibuprofen utilizing the same commercially available inexpensive resolving agent, (S)-lysine. The unwanted enantiomeric ibuprofen could be recovered from the mother liquor and racemized by a simple, relatively waste-free thermal process. This racemization method when utilized in conjunction with the selective crystallization technology provides a simple, efficient, and eco-friendly means to prepare (S)-(+)-ibuprofen lysinate in an overall essentially quantitative yield. This technology also incorporates the fundamental principle of atom economy (via direct production of the preferred pharmaceutical salt of (S)-lysine). Abstract Image 

Temperature Selective Diastereo-Recognition (TSD):  Enantiomeric Ibuprofen via Environmentally Benign Selective Crystallization

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