Water → 2-(4-Methoxybenzyl)-2h-tetrazole-5-carboxylic acid

HRID 881871Notes

Reaction equation

HRID 881871 reaction equation
[Na].C([O:4][C:5]([C:7]1[NH:11][N:10]=[N:9][N:8]=1)=[O:6])C.[CH3:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Cl)=[CH:16][CH:15]=1.O.[OH-].[Na+]>CN(C=O)C.CCO>[CH3:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][N:10]2[N:9]=[N:8][C:7]([C:5]([OH:4])=[O:6])=[N:11]2)=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 699934-Methyloxybenzyl chlorideHCID 178470519HCID 178470519, compound

Product 1

HCID 135962442-(4-Methoxybenzyl)-2h-tetrazole-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1H-tetrazole-5-carboxylic acid ethyl ester sodium salt (500 mg, 3.05 mmol) in DMF (5 ml) at room temperature is added 4-methoxybenzyl chloride (747 μl, 5.48 mmol) and TEA (1500 μl, 10.76 mmol). The reaction mixture is stirred at room temperature overnight. The reaction is added water and extracted with EtOAc. The combined organic layer is washed with brine and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue is purified by column chromatography (10% to 30% EtOAc/Heptane). To a solution of the purified residue in EtOH (2 ml) at room temperature is added NaOH (2 ml, 2.000 mmol) and the mixture is stirred at room temperature. After stirring for 1 hour, the mixture is concentrated under reduced pressure to remove EtOH and extracted with EtOAC after being acidified to pH<5. The combined organic layer is washed with brine and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 2-(4-methoxy-benzyl)-2H-tetrazole-5-carboxylic acid.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic layer is washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by column chromatography (10% to 30% EtOAc/Heptane)
  7. stirringthe mixture is stirred at room temperature
  8. stirringAfter stirring for 1 hour
  9. concentrationthe mixture is concentrated under reduced pressure
  10. customto remove EtOH
  11. extractionextracted with EtOAC
  12. washThe combined organic layer is washed with brine
  13. dry with materialdried over anhydrous sodium sulfate
  14. filtrationfiltered
  15. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8768db45d5a846db8166e4c8734085b4
Source dataset
uspto-grants-2015_03
Patent number
US08993631B2

Reaction notes

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