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Synfacts 2010(3): 0265-0265  
DOI: 10.1055/s-0029-1219296
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of a Glycine Antagonist

Contributor(s): Philip Kocienski
J. S. Carey et al.*
GlaxoSmithKline Pharmaceuticals, Tonbridge and Stevenage, UK and GlaxoSmithKline Pharmaceuticals, Verona, Italy
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Publication History

Publication Date:
18 February 2010 (online)

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Significance

The target molecule is an orally available glycine antagonist that is under development for the treatment of nicotine craving. The route depicted produced more than 300 kg of the target with a purity of >99.9%. The high efficiency of the enzymatic resolution of rac-F (E > 500) using an immobilized lipase from Mucor miehei was further enhanced by the easy recycling afforded by the epimerization of the unwanted enantiomer (S)-F. A total of 600 kg of (R)-F with a chiral purity of 99.7% was prepared by this route.