Phosphonic dichloride, (4-chlorophenyl)- → (2R,3S,4S,5R)-2-(4-amino-2-oxopyrimidin-1(2H)-yl)-4-(benzyloxy)-5-(benzyloxymethyl)-5-(difluoromethyl)-tetrahydrofuran-3-yl acetate

HRID 2205186

Reaktionsgleichung

Reaktionsgleichung von HRID 2205186
ClC1C=CC(P(Cl)(Cl)=O)=CC=1.[NH:12]1C=NN=N1.[C:17]([O:20][C@H:21]1[C@H:25]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C@:24]([CH2:37][O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)([CH:34]([F:36])[F:35])[O:23][C@H:22]1[N:46]1[CH:51]=[CH:50][C:49](=O)[NH:48][C:47]1=[O:53])(=[O:19])[CH3:18]>N1C=CC=CC=1>[C:17]([O:20][C@H:21]1[C@H:25]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C@:24]([CH2:37][O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)([CH:34]([F:35])[F:36])[O:23][C@H:22]1[N:46]1[CH:51]=[CH:50][C:49]([NH2:12])=[N:48][C:47]1=[O:53])(=[O:19])[CH3:18]

Komponenten

5

Edukt 3

HCID 2724255Phosphonic dichloride, (4-chlorophenyl)-HCID 118294157(2R,3S,4S,5R)-4-(benzyloxy)-5-(benzyloxymethyl)-5-(difluoromethyl)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-tetrahydrofuran-3-yl acetateHCID 178418441HCID 178418441, Verbindung

Produkt 1

HCID 118294215(2R,3S,4S,5R)-2-(4-amino-2-oxopyrimidin-1(2H)-yl)-4-(benzyloxy)-5-(benzyloxymethyl)-5-(difluoromethyl)-tetrahydrofuran-3-yl acetateAusbeute 176,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

4-Chlorophenylphosphonic dichloride (0.4 g, 0.81 mmol) was added to a cooled (0° C.) solution of 1-H-tetrazole (0.056 g, 0.81 mmol) and 35 (0.113 g, 0.22 mmol) in dry pyridine (5 mL). The reaction mixture was left to stir under a nitrogen atmosphere at 20° C. for 3 h and then evaporated to dryness under reduced pressure. The residue was dissolved in dioxane and NH3.H2O (5 mL) was added. After stirring for 5 h at 20° C., the reaction mixture was evaporated to dryness under reduced pressure to afford 36 (0.2 g, crude).

Aufarbeitung

  1. waitThe reaction mixture was left
  2. customevaporated to dryness under reduced pressure
  3. dissolutionThe residue was dissolved in dioxane
  4. additionNH3.H2O (5 mL) was added
  5. stirringAfter stirring for 5 h at 20° C.
  6. customthe reaction mixture was evaporated to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6229a69b08c545c49359192255d7315e
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09370569B2

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