The synthesis of GW710936X to support the development of potent PPARγ agonists

(2S)-[(2-Benzoyl-4-hydroxy-phenyl)amino]-3-{4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenyl}propanoic acid has been synthesised from N-Cbz-l-tyrosine methyl ester utilising a copper(I) catalysed N-arylation as the key coupling step. The synthetic route was designed to be convergent and to facilitate ease of isolation of the unstable product that had proven to be unobtainable by concentration of extracts from biological assays.