Methanol → 3-[5-(1,1-Difluoro-ethyl)-tetrazol-1-yl]-5-(5-methyl-pyridin-2-yl)-benzoic acid

HRID 553800Notes

Reaction equation

HRID 553800 reaction equation
C[O:2][C:3](=[O:26])[C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][N:11]=2)[CH:7]=[C:6]([N:17]2[C:21]([C:22]([F:25])([F:24])[CH3:23])=[N:20][N:19]=[N:18]2)[CH:5]=1.CO.[OH-].[Na+]>C(Cl)Cl>[F:24][C:22]([C:21]1[N:17]([C:6]2[CH:5]=[C:4]([CH:9]=[C:8]([C:10]3[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][N:11]=3)[CH:7]=2)[C:3]([OH:26])=[O:2])[N:18]=[N:19][N:20]=1)([F:25])[CH3:23]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 666640383-[5-(1,1-Difluoro-ethyl)-tetrazol-1-yl]-5-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester

Product 1

HCID 666643303-[5-(1,1-Difluoro-ethyl)-tetrazol-1-yl]-5-(5-methyl-pyridin-2-yl)-benzoic acidYield 235.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-[5-(1,1-Difluoro-ethyl)-tetrazol-1-yl]-5-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester (0.605 g, 0.68 mmol) was added to a mixture of methanol (10 mL), methylene chloride (2 mL) and 3N aqueous NaOH (0.5 mL). The reaction mixture was stirred at room temperature for 18 hours, then solvent was removed under reduced pressure. The liquid residue was diluted with water and acidified to pH 5 by addition of 1N aqueous HCl. The resulting mixture was extracted with EtOAc, and the combined organic layers were washed with water, dried (MgSO4), filtered and concentrated under reduced pressure to give 0.552 g of 3-[5-(1,1-Difluoro-ethyl)-tetrazol-1-yl]-5-(5-methyl-pyridin-2-yl)-benzoic acid.

Workup

  1. customsolvent was removed under reduced pressure
  2. additionThe liquid residue was diluted with water
  3. additionacidified to pH 5 by addition of 1N aqueous HCl
  4. extractionThe resulting mixture was extracted with EtOAc
  5. washthe combined organic layers were washed with water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-acf5de8d7cc744189350f0026413574e
Source dataset
uspto-grants-2011_11
Patent number
US08048905B2

Reaction notes

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