Reaction Steps
2-(4-{3-[1-(Phenylmethyl)-5-oxo-4,5-dihydro-1H-[1,2,4]triazol-3-yl]-propyl}-phenoxy)-2-methylpropionic acid ethyl ester (557 mg, 1.20 mmol) was dissolved in ethanol (5 mL) and 1N aq. NaOH (3.6 mL, 3.6 mmol) was added in one portion and the solution was stirred at room temperature for 16 h. The solution was then concentrated to a hazy colorless oil. This oil was diluted with water (5 mL) and washed with t-butyl methyl ether (5 mL). The pH of the aqueous layer was adjusted to <1with conc. HCl and the aqueous was extracted with ethyl acetate (10 mL, then 5 mL). This solution was washed with 1 N aqueous HCl (5 mL) and sat'd aq. NaCl (5 mL), dried (MgSO4), and concentrated in vacuo to afford the title compound as a clear colorless oil (442 mg, 84.5%). 1H NMR (DMSO-d6) δ 12.9 (br s, 1H), 7.30 (t, 2H, J=7 Hz), 7.25 (d, 1H, J=7 Hz), 7.20 (d, 2H, J=7 Hz), 7.04 (d, 2H J=8 Hz), 6.72 (d, 2H, J=8 Hz), 4.83 (s, 2H), 3.47 (t, 2H, J=7 Hz), 2.54 (t, 2H, J=8 Hz), 2.49 (t, 2H, J=8 Hz), 1.83 (quint, 2H, J=7 Hz), 1.53, (m, 2H), 1.46 (s, 6H), 0.80 (t, 3H, J=7 Hz); 13C NMR (DMSO-d6) δ 175.8, 154.1, 146.0, 138.1, 135.2, 129.7, 129.2, 128.0, 119.3, 79.0, 48.5, 42.8, 34.0, 27.9, 25.7, 24.8, 22.5, 11.5; IR (CHCl3) 2938, 1509, 1468, 1233, 1155 cm−1; Anal. Calcd. For C25H31N3O4: C, 68.63; H, 7.14; N, 9.60. Found: C, 68.24; H, 6.95; N, 9.40.
