Reaction Steps
2-(4-{3-[1-(4-t-Butylbenzyl)-4-methyl-5-oxo-4,5-dihydro-1H-[1,2,4]triazol-3-yl]-propyl}-phenoxy)-2-methyl-propionic acid ethyl ester (0.69 g, 1.39 mmol) was dissolved in ethanol (4 mL)), 1 N NaOH (4.75 mL) was added in one portion and the solution was stirred at ambient temperature overnight. The solution was concentrated to a hazy, colorless oil. This oil was partitioned between 1N HCl (5 mL) and ethyl acetate (5 mL). The aqueous layer was then reextracted with ethyl acetate (5 mL) and the organic layers combined, dried (MgSO4), filtered and concentrated in vacuo at 50° C. to afford the title compound as a clear oil (0.56 g, 86%): 1H NMR (DMSO-d6) δ 12.9 (br s, 1H), 7.31 (d, 2H, J=6 Hz), 7.14 (d, 2H, J=8 Hz), 7.05 (d, 2H, J=7 Hz), 6.73 (d, 2H, J=2 Hz), 4.77 (s, 2H), 3.09 (s, 3H), 2.53 (t, 2H, J=8 Hz), 2.49 (t, 2H, J=8 Hz), 1.81 (quint, 2 H, J=7 Hz), 1.46 (s, 6H), 1.22 (s, 9H); 13C NMR (DMSO-d6) δ 175.8, 154.14, 154.10, 150.5, 147.2, 135.2, 135.0, 129.7, 128.0, 125.9, 119.2, 79.0, 48.3, 34.9, 34.1, 31.8, 27.7, 27.6, 25.7, 25.1; IR (CHCl3) 2966, 1695, 1509, 1235 cm−1; Anal. Calcd. for C27H35N3O4: C, 69.65; H, 7.58; N, 9.02. Found: C, 69.30; H, 7.30; N, 8.96.
