Ethyl Acetate → (2R,3R)-2-(2,4-Difluorophenyl)-3-(1H-1,2,4-triazol-1-yl)-3-[[1-(tert-butoxycarbonyl)piperidin-4-yl]thio]-2-butanol

HRID 1601361

Reaktionsgleichung

Reaktionsgleichung von HRID 1601361
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([SH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[F:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[C@@:25]1([CH2:29][N:30]2[CH:34]=[N:33][CH:32]=[N:31]2)[C@H:27](C)[O:26]1.[C:35](OCC)(=O)C>CN(C)C=O>[F:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[C@@:25]([OH:26])([C@:29]([N:30]1[CH:34]=[N:33][CH:32]=[N:31]1)([S:14][CH:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]1)[CH3:35])[CH3:27]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 101311911-((2-(2,4-Difluorophenyl)-3-methyloxiran-2-yl)methyl)-1H-1,2,4-triazole, (2R-cis)-HCID 21906090tert-Butyl 4-sulfanylpiperidine-1-carboxylate

Produkt 1

HCID 53773004(2R,3R)-2-(2,4-Difluorophenyl)-3-(1H-1,2,4-triazol-1-yl)-3-[[1-(tert-butoxycarbonyl)piperidin-4-yl]thio]-2-butanolAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In 6 ml of dimethylformamide was dissolved 1-(tert-butoxycarbonyl)-4-mercaptopiperidine (corresponding to 2 mmol) as described in Reference example 12, and 86 mg (1.97 mmol) of 55% sodium hydride were added to the solution at 0° C. under a nitrogen atmosphere, followed by stirring of the resulting mixture at the same temperature for 20 minutes. Then, 503 mg (2.00 mmol) of (2R,3S)-2-(2,4-difluorophenyl)-3-methyl-2-[(1H-1,2,4-triazol-1-yl)methyl]oxirane were added to the reaction mixture and the mixture was stirred at 60° C. for 3 hours. After cooling, ethyl acetate was added to the reaction mixture to dilute it and washed successively with water and a saturated aqueous NaCl solution. An oil obtained by evaporation of the solvent was subjected to silica gel column chromatography and eluted with ethyl acetate to obtain 557 mg (yield: 53%) of the desired compound as an oil.

Aufarbeitung

  1. additionwere added to the solution at 0° C. under a nitrogen atmosphere
  2. stirringthe mixture was stirred at 60° C. for 3 hours
  3. temperatureAfter cooling
  4. additionto dilute it
  5. washwashed successively with water
  6. customAn oil obtained by evaporation of the solvent
  7. washeluted with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-4b84ce05921c47c1b55748331cb6f5df
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05977152

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