Hydrochloric Acid → HCID 57889538, compound

Reaction equation

[CH2:1]([O:8][CH2:9][N:10]1[N:14]=[N:13][C:12]([C:15]2[CH:16]=[C:17]([CH:23]=[CH:24][CH:25]=2)[C:18]([O:20]CC)=[O:19])=[N:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+].Cl>C1COCC1>[CH2:1]([O:8][CH2:9][N:10]1[N:14]=[N:13][C:12]([C:15]2[CH:16]=[C:17]([CH:23]=[CH:24][CH:25]=2)[C:18]([OH:20])=[O:19])=[N:11]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Procedure

A solution of ethyl 3-(2-(benzyloxymethyl)-2H-tetrazol-5-yl)benzoate (653 mg, 1.93 mmol) in THF (10 mL) was treated with a 0.5 M aqueous lithium hydroxide solution (5.8 mL, 2.9 mmol), and the reaction was stirred for about 16 hours. After this time, analysis by LC/MS indicated that the reaction had not gone to completion. As such, the mixture was treated with additional 0.5 M aqueous lithium hydroxide solution (1 mL, 0.5 mmol), and the reaction was stirred for an additional 6 hours. After this time, the THF was removed under reduced pressure, and the aqueous solution was treated with 1 N HCl (3.5 mL, 3.5 mmol). The resulting mixture was extracted 3× with ethyl acetate, and the combined organic phases were dried over sodium sulfate and concentrated in vacuo to yield 3-(2-(benzyloxymethyl)-2H-tetrazol-5-yl)benzoic acid as a colorless powder, which was used as-is in the next step.