[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]([O:15]CC)=[O:14])=[CH:11][N:10]=[C:9]2[SH:18])=[CH:4][CH:3]=1.[OH-].[Li+]>O1CCOCC1.CO.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([C:13]([OH:15])=[O:14])=[CH:11][N:10]=[C:9]2[SH:18])=[CH:6][CH:7]=1To a solution of ethyl 1-(4-fluorophenyl)-2-mercapto-1H-imidazole-5-carboxylate (3) (2.62 g, 9.84 mmol) in 1,4-dioxane (21 mL) and methanol (10 mL) was added lithium hydroxide (825 mg, 19.7 mmol) in water (21 mL). The reaction was stirred at 50° C. overnight and the organic solvents were removed in vacuo. The mixture was acidified with 1M HCl until a white solid crashed out of the solution. The solid was collected by vacuum filtration and washed with water to afford 1-(4-fluorophenyl)-2-mercapto-1H-imidazole-5-carboxylic acid (4).
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