[CH2:1]([N:8]1[C:12]([C:13]2[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[CH:15][C:14]=2F)=[N:11][N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][O-:24].[Na+]>C(Cl)Cl.CO>[CH2:1]([N:8]1[C:12]([C:13]2[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[CH:15][C:14]=2[O:24][CH3:23])=[N:11][N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=11-Benzyl-5-(2-fluoro-6-nitrophenyl)-1H-tetrazole (Intermediate 18, 0.3 g) was dissolved in DCM (4 mL) and a solution of sodium methoxide in methanol (20%; 2 mL) was added. The mixture was stirred for 4 hours and then the solvent was removed by evaporation under vacuum. The residue was dissolved in ethyl acetate and washed with 1N hydrochloric acid and then brine. The organic solution was dried with sodium sulfate, filtered and the solvent was removed by evaporation under vacuum. The residue was purified by flash chromatography on silica, eluting with a mixture of DCM and methanol. The fractions containing the desired product were combined and evaporated to give the title compound as a pale yellow solid (0.14 g).
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