To a cooled (0° C. ice bath) solution of triphenylphosphine (392 mg, 1.495 mmol) in THF (10 mL) was added DIAD (0.291 mL, 1.495 mmol). The reaction was stirred for 15 minutes (became a suspension). To this suspension with stirring was added a solution of methyl 5-chloro-3-hydroxy-2-methylbenzoate (250 mg, 1.246 mmol) and (cis)-N -benzyl-4-hydroxycyclohexanecarboxamide (350 mg, 1.500 mmol) in THF (5 mL) in one portion. The reaction was allowed to warm to room temperature and stirred overnight, at which time the reaction was concentrated in vacuo. The residue was purified by silica gel chromatography (Analogix, SF25-60 g, 10 to 60% EtOAc in hexanes). The resulting solid was triturated with 10% methanol in water, filtered, washed with water, and dried under vacuum to give methyl 3-(((trans)-4-(benzylcarbamoyl)cyclohexyl)oxy)-5-chloro-2-methylbenzoate (180 mg, 0.433 mmol, 34.7% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.33 (t, J=5.94 Hz, 1H), 7.38 (d, J=2.02 Hz, 1H), 7.27-7.35 (m, 3H), 7.16-7.27 (m, 3H), 4.37-4.49 (m, 1H), 4.27 (d, J=5.81Hz, 2H), 3.82 (s, 3H), 2.25 (s, 3H), 1.97-2.16 (m, 3H), 1.75-1.89 (m, 2H), 1.53-1.69 (m, 2H), 1.30-1.47 (m, 2H). MS(ES) [M+H]+ 259.0 (weak).
