O.[OH-].[Li+].[CH3:4][C:5]1[C:10]([N:11]2[CH:15]=[N:14][N:13]=[N:12]2)=[CH:9][N:8]=[C:7]([CH2:16][C:17]([O:19]C)=[O:18])[CH:6]=1.Cl>O.O1CCCC1>[CH3:4][C:5]1[C:10]([N:11]2[CH:15]=[N:14][N:13]=[N:12]2)=[CH:9][N:8]=[C:7]([CH2:16][C:17]([OH:19])=[O:18])[CH:6]=1Lithium hydroxide monohydrate (19.2 mg, 0.458 mmol) was dissolved in 5 mL water then added to a methyl 2-(4-methyl-5-(1H-tetrazol-1-yl)pyridin-2-yl)acetate in tetrahydrofuran (15 mL). The reaction was stirred for 1 h then acidified with 1 N HCl to pH ˜3. The mixture was extracted with a mixture of THF/ethyl acetate (4×.). Dried over Na2SO4, filtered and evaporated concentrated to yield 2-(4-methyl-5-(1H-tetrazol-1-yl)pyridin-2-yl)acetic acid.
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