(Diethylamino)sulfur trifluoride → 1-((2R,3R,4R,5R)-4-(benzyloxy)-5-(benzyloxymethyl)-5-(difluoromethyl)-3-fluoro-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

HRID 2205189Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2205189
C(N(S(F)(F)[F:7])CC)C.[CH2:10]([O:17][C@@H:18]1[C@:22]([CH2:26][O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([CH:23]([F:25])[F:24])[O:21][C@@H:20]([N:35]2[CH:40]=[CH:39][C:38](=[O:41])[NH:37][C:36]2=[O:42])[C@H:19]1O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1COCC1>[CH2:10]([O:17][C@@H:18]1[C@:22]([CH2:26][O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([CH:23]([F:25])[F:24])[O:21][C@@H:20]([N:35]2[CH:40]=[CH:39][C:38](=[O:41])[NH:37][C:36]2=[O:42])[C@@H:19]1[F:7])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Komponenten

4

Edukt 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 1182943391-((2R,3S,4S,5R)-4-(Benzyloxy)-5-((benzyloxy)methyl)-5-(difluoromethyl)-3-hydroxytetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

Produkt 1

HCID 1182942631-((2R,3R,4R,5R)-4-(benzyloxy)-5-(benzyloxymethyl)-5-(difluoromethyl)-3-fluoro-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dioneAusbeute 46,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Diethylaminosulfur trifluoride (7.6 g, 47.4 mmol) was added to a suspension of compound 34 (1.5 g, 3.16 mmol) in dry THF (150 mL). The mixture was stirred at 60° C. for 16 h and then cooled to room temperature. The mixture was quenched by the addition of saturated aqueous NaHCO3 solution and then extracted with ethyl acetate. The organic phase was washed with brine, dried (Na2SO4) and evaporated to dryness under reduced pressure. Purification by silica gel chromatography [petroleum ether:ethyl acetate (4:1)] afforded 39 as a brown solid (700 mg, 46%). LC-MS (M+H)+=477.4

Aufarbeitung

  1. temperaturecooled to room temperature
  2. customThe mixture was quenched by the addition of saturated aqueous NaHCO3 solution
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated to dryness under reduced pressure
  7. customPurification by silica gel chromatography [petroleum ether:ethyl acetate (4:1)]

Quellen und Nachweise

ORD-Eintrag
ord-9761056fa149470eb32c13013911d9ca
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09370569B2

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