O1CCOCC1.[OH-].[K+].C(N(CC)[C:12](=[O:30])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH:19]([N:24]1[C:28]([I:29])=[CH:27][N:26]=[CH:25]1)[C:20]([OH:23])([CH3:22])[CH3:21])C.Cl>C(OCC)(=O)C>[I:29][C:28]1[N:24]([CH:19]2[C:14]3[C:13](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:12](=[O:30])[O:23][C:20]2([CH3:22])[CH3:21])[CH:25]=[N:26][CH:27]=1Dioxane (22 mL) and 1M aqueous KOH (22 mL, 22 mmol) are added to N,N-diethyl-2-[2-hydroxy-1-(5-iodo-imidazol-1-yl)-2-methyl-propyl]-benzamide (1.65 g) and the mixture is heated to 60° C. After 13.5 h, the mixture is cooled to 0° C. and acidified to pH=1 with conc. HCl. The mixture is heated to 60° C. After 24 h, the mixture is diluted with ethyl acetate and washed with saturated aqueous sodium bicarbonate, water and brine, dried over magnesium sulfate and filtered through a cotton plug. Concentration in vacuo gave an orange solid, which is purified by silica gel flash chromatography (methylene chloride-methanol, 49:1) to give a crystalline yellow solid; MS (ESI) m/z 369.0 (M+H); 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.30 (s, 3 H), 1.57 (s, 3 H), 5.39 (s, 1 H), 7.19 (s, 1 H), 7.28 (br. d, J=7.6 Hz, 1 H), 7.39 (s, 1 H), 7.59 (td, J=7.6, 1.3 Hz, 1 H), 7.66 (td, J=7.6, 1.3 Hz, 1H), 8.27 (dd, J=7.6, 1.4 Hz, 1 H).
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