Lithium Hydroxide → HCID 67517682, compound

HRID 2173383Notes

Reaction equation

HRID 2173383 reaction equation
[N:1]1([C:6]2[N:11]=[C:10]([CH2:12][C:13]([O:15]C)=[O:14])[CH:9]=[CH:8][CH:7]=2)[CH:5]=[N:4][N:3]=[N:2]1.[OH-].[Li+]>C1COCC1>[N:1]1([C:6]2[N:11]=[C:10]([CH2:12][C:13]([OH:15])=[O:14])[CH:9]=[CH:8][CH:7]=2)[CH:5]=[N:4][N:3]=[N:2]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 77230640HCID 77230640, compound

Product 1

HCID 67517682HCID 67517682, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl [6-(1H-tetrazol-1-yl)pyridin-2-yl]acetate (367 mg, 1.67 mmol) in THF (5 mL) was added 1.5 mL of 1N aqueous lithium hydroxide solution. The reaction mixture was allowed to stir at ambient temperature for 30 minutes and then concentrated in vacuo. The crude residue was dissolved in 4 mL of a 1N aqueous hydrochloric acid solution and extracted with DCM (3×20 mL). The combined organic layers were then dried over sodium sulfate, filtered and concentrated in vacuo to afford crude [6-(1H-tetrazol-1-yl) pyridin-2-yl]acetic acid which was used without further purification. LC/MS (M+H−28)+178.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe crude residue was dissolved in 4 mL of a 1N aqueous hydrochloric acid solution
  3. extractionextracted with DCM (3×20 mL)
  4. dry with materialThe combined organic layers were then dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-757da26b778945bfb471bcfbfd6d0238
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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