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

HRID 84757

Reaktionsgleichung

Reaktionsgleichung von HRID 84757
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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 666643303-[5-(1,1-Difluoro-ethyl)-tetrazol-1-yl]-5-(5-methyl-pyridin-2-yl)-benzoic acidAusbeute 235,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-eeda0e198abb4cc29fd32eb67b681fe2
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846945B2

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