Water → HCID 22320692, Verbindung

HRID 498084Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 498084
[C:1]([N:5]([C:14]1[CH:28]=[CH:27][C:17]([C:18]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)=[O:19])=[CH:16][CH:15]=1)[O:6][Si](C(C)(C)C)(C)C)([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C([O-])(O)=O.[Na+]>C1COCC1.C(OCC)(=O)C>[C:1]([N:5]([C:14]1[CH:28]=[CH:27][C:17]([C:18]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)=[O:19])=[CH:16][CH:15]=1)[OH:6])([CH3:4])([CH3:2])[CH3:3]

Komponenten

7

Edukt 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 22320676HCID 22320676, Verbindung

Produkt 1

HCID 22320692HCID 22320692, VerbindungAusbeute 65,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 0.95 g (2.37 mmol) of compound 5 in THF (3 mL) was added 2.84 mL (2.84 mmol) of 1 M solution of tetrabutylammonium fluoride in THF at room temperature, and the solution was stirred for 1 hour. After completion of the reaction, 2 mL of water was added to quench the reaction. Ethyl acetate and sat'd NaHCO3 solution were added to the mixture, and the organic layer was separated, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica, Hex:EtOAc=10:1) to give 0.44 g of compound 6 in 65% yield.

Aufarbeitung

  1. additionwas added
  2. customto quench
  3. customthe reaction
  4. additionwere added to the mixture
  5. customthe organic layer was separated
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash column chromatography (silica, Hex:EtOAc=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-97a09f27897e4f41907a7aeca41e545c
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06949654B2

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