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

HRID 1610474Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1610474
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([CH:15]([OH:26])[C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)[C:10]([O:12]CC)=[O:11])=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH:9]([CH:15]([OH:26])[C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:24])([F:25])[F:23])=[CH:18][CH:17]=2)[C:10]([OH:12])=[O:11])=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22261474ethyl(2RS,3RS)-2-((4-fluorophenyl)methyl)-3-hydroxy-3-(4-(trifluoromethyl)phenyl)propionate

Produkt 1

HCID 17862204(2RS,3RS)-2-((4-fluorophenyl)methyl)-3-hydroxy-3-(4-(trifluoromethyl)phenyl)propionic acidAusbeute 88,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of ethyl(2RS,3RS)-2-((4-fluorophenyl)methyl)-3-hydroxy-3-(4-(trifluoromethyl)phenyl)propionate (27.5 g, 74.3 mmol) in methanol (300 ml) was added 1N aqueous sodium hydroxide solution (150 ml, 150 mmol), and the mixture was stirred overnight at room temperature. The reaction solution was poured into 1N aqueous hydrochloric acid solution (180 ml), and the mixture was extracted with ethyl acetate (300 ml×2). The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. Recrystallization of the residue from ethyl acetate-hexane gave (2RS,3RS)-2-((4-fluorophenyl)methyl)-3-hydroxy-3-(4-(trifluoromethyl)phenyl)propionic acid (22.45 g, 88%).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate (300 ml×2)
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customRecrystallization of the residue from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-0d4f0c10a0f64297b8685b214f04ecc4
Quelldatensatz
uspto-grants-2006_01
Patentnummer
US06982348B2

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