HCID 86607298, Verbindung → HCID 86607329, Verbindung

HRID 552755Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 552755
[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[O:21][C@H:20]2[C@@H:13]([O:14][Si](C(C)C)(C(C)C)O[Si](C(C)C)(C(C)C)[O:18][CH2:19]2)[C@@H:12]1[O:34][CH3:35]>C1COCC1.N1C=CC=CC=1.F.N1C=CC=CC=1.CCOC(C)=O>[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[O:21][C@H:20]([CH2:19][OH:18])[C@@H:13]([OH:14])[C@@H:12]1[O:34][CH3:35]

Komponenten

6

Edukt 1

HCID 86607298HCID 86607298, Verbindung

Produkt 1

HCID 86607329HCID 86607329, VerbindungAusbeute 95,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 14917Hydrofluoric AcidKatalysatorHCID 1049PyridineLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 16069498Pyridine tetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 6-chloro-9-[(6aR,8R,9S,9aR)-2,2,4,4-tetraisopropyl-9-methoxytetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-9H-purine (1.31 g, 2.41 mmol) in THF/pyridine (12 mL, 1:1) was added approximately 20 drops of hydrofluoric acid in pyridine. This solution was stirred at r.t. overnight. The reaction was diluted with EtOAc (10 mL) and quenched with saturated aq NaHCO3. The aq layer was extracted with EtOAc (3×40 mL) and the combined organics were dried (Na2SO4), filtered, and concentrated. The crude material was purified by flash chromatography (0 to 10% MeOH/DCM) to afford the title compound (0.690 g, 74%).

Aufarbeitung

  1. customquenched with saturated aq NaHCO3
  2. extractionThe aq layer was extracted with EtOAc (3×40 mL)
  3. dry with materialthe combined organics were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by flash chromatography (0 to 10% MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-ae290d9c4ccc44ac9bd955fc5dc43218
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07951810B2

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