A solution of (±)-2-cyclohexyl-1-(4′-trifluoromethyl-biphenyl-4-yl)-ethanol (0.184 g, 0.527 mmol), 3-(4-hydroxy-benzoylamino)-propionic acid methyl ester (0.136 g, 0.608 mmol), and triphenylphosphine (0.208 g, 0.791 mmol) in toluene (8.0 mL) is treated with 1,1′-(azodicarbonyl)dipiperidine (ADDP, 0.206 g, 0.817 mmol) and stirred overnight. The reaction mixture is filtered through Celite® diluted with EtOAc, washed with water (2×), brine (1×), dried over MgSO4, filtered, and conc. The residue is loaded onto silica gel and eluted with hexanes using a gradient of 25% EtOAc to 100% EtOAc giving (±)-3-{4-[2-cyclohexyl-1-(4′-trifluoromethyl-biphenyl-4-yl)-ethoxy]-benzoylamino}-propionic acid methyl ester (0.091 g, 31%) as a white foam. MS (ES): 554.0 [M+H]+.
