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Water → (4RS,5SR)-5-(4-fluorophenyl)-4-((5-(trifluoromethyl)-2-furanyl)methyl)-1,3-oxazolidine-2-one

HRID 1610332
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1610332
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:23])[CH:9]([CH2:13][C:14]2[O:15][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:18]=2)C(O)=O)=[CH:4][CH:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C([N:43]([CH2:46]C)CC)C.[OH2:48]>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[O:23][C:46](=[O:48])[NH:43][CH:9]2[CH2:13][C:14]2[O:15][C:16]([C:19]([F:20])([F:21])[F:22])=[CH:17][CH:18]=2)=[CH:6][CH:7]=1
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Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 22261402(2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-((5-(trifluoromethyl)-2-furanyl)methyl)propionic acid

Produkt 1

HCID 22261763(4RS,5SR)-5-(4-fluorophenyl)-4-((5-(trifluoromethyl)-2-furanyl)methyl)-1,3-oxazolidine-2-oneAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-((5-(trifluoromethyl)-2-furanyl)methyl)propionic acid (2.33 g, 7.01 mmol) in tetrahydrofuran (60 ml) were added diphenylphosphoryl azide (1.66 ml, 7.71 mmol) and triethylamine (1.47 ml, 10.5 mmol) and the mixture was heated under reflux for 4 hrs. The reaction solution was allowed to stand at room temperature, water (50 ml) was added, and the mixture was extracted with ethyl acetate (100 ml×2). The extract was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) and recrystallized from ethyl acetate-hexane to give (4RS,5SR)-5-(4-fluorophenyl)-4-((5-(trifluoromethyl)-2-furanyl)methyl)-1,3-oxazolidine-2-one (1.78 mg, 77%).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hrs
  3. customto stand at room temperature
  4. extractionthe mixture was extracted with ethyl acetate (100 ml×2)
  5. washThe extract was washed successively with water 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. customrecrystallized from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-4af3deb38081428384fcf0bce2ba2acb
Quelldatensatz
uspto-grants-2006_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06982348B2

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