Hydrochloric Acid → 2-(Allyloxy)-6-{[(4'-{[(allyloxy)carbonyl]methyl}-3-fluoro-1,1'-biphenyl-4-yl)oxy]methyl}-3-(trifluoromethyl)benzoic acid

HRID 2076605

반응식

HRID 2076605 반응식
Cl([O-])=O.[Na+].O.P([O-])(O)(O)=O.[Na+].[CH2:12]([O:15][C:16]1[C:17]([CH:48]=[O:49])=[C:18]([CH:41]=[CH:42][C:43]=1[C:44]([F:47])([F:46])[F:45])[CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][C:30]([CH2:33][C:34]([O:36][CH2:37][CH:38]=[CH2:39])=[O:35])=[CH:29][CH:28]=2)=[CH:23][C:22]=1[F:40])[CH:13]=[CH2:14].CC(=CC)C.S([O-])([O-])(=[O:57])=S.[Na+].[Na+].Cl>C(O)(C)(C)C.O1CCOCC1>[CH2:12]([O:15][C:16]1[C:43]([C:44]([F:46])([F:47])[F:45])=[CH:42][CH:41]=[C:18]([CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:28]=[CH:29][C:30]([CH2:33][C:34]([O:36][CH2:37][CH:38]=[CH2:39])=[O:35])=[CH:31][CH:32]=3)=[CH:23][C:22]=2[F:40])[C:17]=1[C:48]([OH:57])=[O:49])[CH:13]=[CH2:14]

참가 물질

9

반응물 6

HCID 313Hydrochloric AcidHCID 105532-Methyl-2-buteneHCID 24477Sodium ThiosulfateHCID 516949Sodium Phosphate, Monobasic, MonohydrateHCID 23668197Sodium ChloriteHCID 86617403Allyl (4'-{[3-(allyloxy)-2-formyl-4-(trifluoromethyl)benzyl]oxy}-3'-fluoro-1,1'-biphenyl-4-yl)acetate

생성물 1

HCID 671189772-(Allyloxy)-6-{[(4'-{[(allyloxy)carbonyl]methyl}-3-fluoro-1,1'-biphenyl-4-yl)oxy]methyl}-3-(trifluoromethyl)benzoic acid수율 100%

시약·촉매·용매 2

HCID 6386tert-Butanol용매HCID 312751,4-Dioxane용매

실험 절차

After an aqueous solution (1.1 ml) of sodium chlorite (125 mg, 1.38 mmol) and sodium dihydrogenphosphate monohydrate (125 mg, 0.91 mmol) was added dropwise to a solution of allyl (4′-{[3-(allyloxy)-2-formyl-4-(trifluoromethyl)benzyl]oxy}-3′-fluoro-1,1′-biphenyl-4-yl)acetate obtained in Example (12-5) in a mixture of tert-butyl alcohol (2.4 ml), 1,4-dioxane (0.8 ml) and 2-methyl-2-butene (0.8 ml), the mixture was stirred at room temperature for 2 hours. After a 5% aqueous sodium thiosulfate solution was added to the reaction mixture, the mixture was poured into 1N hydrochloric acid and extracted with ethyl acetate (twice). The organic layer was successively washed with water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure to give a residue. The obtained residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate) to give 2-(allyloxy)-6-{[(4′-{[(allyloxy)carbonyl]methyl}-3-fluoro-1,1′-biphenyl-4-yl)oxy]methyl}-3-(trifluoromethyl)benzoic acid (135 mg, yield: 100%).

후처리

  1. extractionextracted with ethyl acetate (twice)
  2. washThe organic layer was successively washed with water
  3. dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customto give a residue
  6. customThe obtained residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate)

출처 및 근거

ORD 기록
ord-d502c9860e664dd8b70dd773575336a1
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07923573B2

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