[CH2:1]([O:3][C:4](=[O:11])[CH2:5][C:6]1[N:7]=[N:8][NH:9][N:10]=1)[CH3:2].I[CH:13]([CH3:15])[CH3:14].[OH-].[Na+].C(OC(=O)CC1N=NN(C(C)C)N=1)C>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:11])[CH2:5][C:6]1[N:10]([CH:13]([CH3:15])[CH3:14])[N:9]=[N:8][N:7]=1)[CH3:2]
To a solution of (2H-tetrazol-5-yl)-acetic acid ethyl ester (2.0 g, 13 mmol) in dimethylformamide (5 mL) was added 2-iodo-propane (11 g, 64 mmol) and sodium hydroxide (2.6 g, 64 mmol) and the solution was stirred at room temperature for 2 h. Ice water was added and the solution was extracted several times with ethyl acetate. The combined organic layers were washed with a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified via silica gel column chromatography to provide a mixture of (2-isopropyl-2H-tetrazol-5-yl)-acetic acid ethyl ester and (1-isopropyl-1H-tetrazol-5-yl)-acetic acid ethyl ester (2 g, 79% yield).
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