Water → (4RS,5SR)-5-(4-fluorophenyl)-4-((3-fluoro-4-(trifluoromethyl)phenyl)methyl)-1,3-oxazolidin-2-one

HRID 1610305Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1610305
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](O)[CH:9]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[C:16]([F:24])[CH:15]=2)C(O)=O)=[CH:4][CH:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:33])C=CC=CC=1.C([N:45]([CH2:48]C)CC)C.[OH2:50]>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:50][C:48](=[O:33])[NH:45][CH:9]2[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:22])([F:21])[F:23])=[C:16]([F:24])[CH:15]=2)=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 22261853(2RS,3RS)-3-(4-fluorophenyl)-2-((3-fluoro-4-(trifluoromethyl)phenyl)methyl)-3-hydroxypropionic acid

Produkt 1

HCID 22261622(4RS,5SR)-5-(4-fluorophenyl)-4-((3-fluoro-4-(trifluoromethyl)phenyl)methyl)-1,3-oxazolidin-2-oneAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (2RS,3RS)-3-(4-fluorophenyl)-2-((3-fluoro-4-(trifluoromethyl)phenyl)methyl)-3-hydroxypropionic acid (7.0 g, 19.4 mmol) in tetrahydrofuran (180 ml) were added diphenylphosphoryl azide (4.6 ml, 21.4 mmol) and triethylamine (4.1 ml, 29.2 mmol) and the mixture was heated under reflux for 6 hrs. The reaction solution was allowed to stand at room temperature, water (200 ml) was added, and the mixture was extracted with ethyl acetate (200 ml×2). The extract was washed successively with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate). The residue was recrystallized from ethyl acetate-hexane to give (4RS,5SR)-5-(4-fluorophenyl)-4-((3-fluoro-4-(trifluoromethyl)phenyl)methyl)-1,3-oxazolidin-2-one (5.26 g, 76%).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 6 hrs
  3. customto stand at room temperature
  4. extractionthe mixture was extracted with ethyl acetate (200 ml×2)
  5. washThe extract was washed successively with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate)
  9. customThe residue was recrystallized from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-3dd384d83b0742558a75e727507069bf
Quelldatensatz
uspto-grants-2006_01
Patentnummer
US06982348B2

Notizen zur Reaktion

Wird geladen…