Reaction Steps
2-(4-{3-[1-(3-Methoxy-benzyl)-5-oxo-4,5-dihydro-1H-[1,2,4]triazol-3-yl]-propyl}-phenoxy)-2-methyl-propionic acid ethyl ester (1.55 g, 3.42 mmol) was dissolved in a mixture of ethanol (7.5 mL) and water (7.5 mL). Solid sodium hydroxide (0.36 g, 8.73 mmol) was added in one portion and the solution was warmed to 70° C. and stirred for 1 h. The solution was cooled to rt and the pH adjusted to 7 with 6N HCl. The solution was concentrated to an oil, which was partitioned between 1N HCl (10 mL) and ethyl acetate (15 mL). The aqueous layer was then reextracted with ethyl acetate (15 mL) and the combined organic layers were dried (MgSO4), filtered and concentrated in vacuo at 50° C. to afford the title compound as an oil (1.41 g, 97.0%). 1H NMR (DMSO-d6) δ 13.0 (broad s, 1 H), 11.47 (s, 1 H), 7.23 (t, 1 H, J=8 Hz), 7.03 (d, 2 H, J=8 Hz), 6.82 (d, 1 H, J=2 Hz), 6.75 (m, 5 H), 4.73 (s, 2 H), 3.70 (s, 3 H), 3.35 (broad s, 1 H), 2.48 (t, 2 H, J=8 Hz), 2.36 (t, 2 H, J=8 Hz), 1.80 (quint, 2 H, J=7 Hz), 1.46 (s, 6 H); 13C NMR (DMSO-d6, 20° C.) δ 175.8, 160.0, 155.0, 154.1, 146.8, 139.8, 135.0, 130.3, 129.7, 120.1, 119.1, 113.8, 113.2, 78.9, 55.6, 47.8, 40.6, 40.5, 34.0, 28.4, 27.5, 26.2, 25.7; IR (CHCl3) 1707, 1603, 1509, 1159 cm−1; Anal. Calcd. for C23H27N3O5: C, 64.93; H, 6.40; N, 9.88. Found: C, 65.02; H, 6.65; N, 9.57.
