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

HRID 217358

반응식

HRID 217358 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a07da560d1fd4798bced4885ef2610cd
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193368B2

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