To a stirred solution of 2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanoic acid (66 mg, 0.18 mmol) and (5-tert-butyl-3′-methylbiphenyl-2-yl)methanamine (113 mg, 0.119 mmol) in acetonitrile were added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (52 mg, 0.270 mmol), 1-hydroxybenzotriazole (36 mg, 0.27 mmol) and triethylamine (0.063 mL, 0.45 mmol). The reaction mixture was stirred for 15 h at room temperature. The residue dissolved in ethyl acetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate was removed in vacuo. The crude was purified by column chromatography. N-((5-tert-Butyl-3′-methylbiphenyl-2-yl)methyl)-2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanamide (example 21) (74 mg) was obtained as 81% yield.
