1H-1,2,4-Triazole → (2S,3R)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butane-2,3-diol

HRID 368899Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 368899
C([O-])([O-])=O.[K+].[K+].[NH:7]1[CH:11]=[N:10][CH:9]=[N:8]1.[F:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[C@@:20]1([O:25][CH2:24]1)[C@H:21]([OH:23])[CH3:22]>CN(C)C=O>[F:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[C@@:20]([OH:25])([C@H:21]([OH:23])[CH3:22])[CH2:24][N:7]1[CH:11]=[N:10][CH:9]=[N:8]1

Komponenten

5

Edukt 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 10867332(2S,3R)-1,2-Epoxy-2-(2,4-difluorophenyl)butan-3-ol2×

Produkt 1

HCID 9816851(2S,3R)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butane-2,3-diolAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To an ice cooled suspension of anhydrous K2CO3 (0.691 g, 0.005 mole) in N,N-dimethylformamide (7 ml), 1H-1,2,4-triazole (0.345, 0.005 mole) was added in small portions under art atmosphere of nitrogen. The mixture was slowly brought to room temperature and a solution of compound 7c (2R, 3S)-3-(2,4-Difluorophenyl)-3,4-epoxy-2-butanol (0.5 g, 0.0025 mole) in N,N-dimethylformamide (1 ml) was added. The resulting mixture was heated at 80° C. for 2 hours. The solvent was removed under reduced pressure and 25 g of crushed ice was added to the residue. The so formed mixture was extracted with ethyl acetate (50 ml, 2×25 ml). The combined organic layers were washed with water (10 ml) brine (25 ml) and dried over MgSO4. The solvent was removed in vacuo and the residue was chromatographed on silica gel. Elution with methanol in chloroform (0% -3%) gave the title compound 9c as an amorphous solid (0.26 g, 38%).

Aufarbeitung

  1. additionwas added in small portions under art atmosphere of nitrogen
  2. customwas slowly brought to room temperature
  3. customThe solvent was removed under reduced pressure and 25 g of crushed ice
  4. additionwas added to the residue
  5. customThe so formed mixture
  6. extractionwas extracted with ethyl acetate (50 ml, 2×25 ml)
  7. washThe combined organic layers were washed with water (10 ml) brine (25 ml)
  8. dry with materialdried over MgSO4
  9. customThe solvent was removed in vacuo
  10. customthe residue was chromatographed on silica gel
  11. washElution with methanol in chloroform (0% -3%)

Quellen und Nachweise

ORD-Eintrag
ord-feb19ed6c85c434cbda9a14ba43464e7
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06133485

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