[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([C:13]([OH:15])=[O:14])=[C:10]([C:16]3[N:20](C)[N:19]=[N:18][N:17]=3)[CH:9]=2)=[CH:4][CH:3]=1.COC(C1SC(C2C=CC(F)=CC=2)=CC=1C1N(C)N=NN=1)=O.[OH-].[Li+]>CO.C1COCC1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:12][C:11]([C:13]([OH:15])=[O:14])=[C:10]([C:16]3[NH:20][N:19]=[N:18][N:17]=3)[CH:9]=2)=[CH:6][CH:7]=15-(4-Fluoro-phenyl)-3-(1-methyl-1H-tetrazol-5-yl)-thiophene-2-carboxylic acid (DNM-143) A solution of 5-(4-fluoro-phenyl)-3-(1-methyl-1H-tetrazol-5-yl)-thiophene-2-carboxylic acid methyl ester (28 mg, 0.088 mmol) and lithium hydroxide (10.5 mg, 0.44 mmol) in 3 mL of methanol, 4.5 mL of THF and 2 mL of H2O was stirred overnight at room temperature. The solvent was removed, and the residue was redissolved in 5 mL of H2O. After being acidified with 1N HCl, the precipitate formed was collected by suction filtration, washed with H2O, and dried under vacuum overnight. 24 mg (90%) of product was obtained as a white solid, mp: 270.0-272.0° C. (decomposed); 1H NMR (DMSO, 500 MHz) δ 7.89 (m, 2H), 7.77 (s, 1H), 7.36 (m, 2H); 13C NMR (DMSO, 125 MHz) δ 163.76, 161.79, 161.46, 150.48, 147.83, 132.96, 128.94, 128.49, 128.45, 128.39, 127.03, 116.56, 116.39, 34.12.
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