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Hydrochloric Acid → (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-((5-(trifluoromethyl)-2-furanyl)methyl)propionic acid

HRID 1610331
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HRID 1610331 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:25])[CH:9]([CH2:15][C:16]2[O:17][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:20]=2)[C:10]([O:12]CC)=[O:11])=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:25])[CH:9]([CH2:15][C:16]2[O:17][C:18]([C:21]([F:22])([F:23])[F:24])=[CH:19][CH:20]=2)[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1
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참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86593231ethyl (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-((5-(trifluoromethyl)-2-furanyl)methyl)propionate

생성물 1

HCID 22261402(2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-((5-(trifluoromethyl)-2-furanyl)methyl)propionic acid수율 80%

시약·촉매·용매 1

HCID 887Methanol
용매

실험 절차

To a solution of ethyl (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-((5-(trifluoromethyl)-2-furanyl)methyl)propionate (3.3 g, 9.16 mmol) in methanol (9.2 ml) was added 2N aqueous sodium hydroxide solution (9.2 ml,18.4 mmol) and the mixture was stirred overnight at room temperature. The reaction solution was acidified with 1N hydrochloric acid and extracted with ethyl acetate (100 ml×2). The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was recrystallized from diisopropyl ether-hexane to give (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-((5-(trifluoromethyl)-2-furanyl)methyl)propionic acid (2.43 g, 80%).

후처리

  1. extractionextracted with ethyl acetate (100 ml×2)
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was recrystallized from diisopropyl ether-hexane

출처 및 근거

ORD 기록
ord-e1c73134db6b45ddba094a217ca7bf0b
출처 데이터셋
uspto-grants-2006_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06982348B2

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