Methanol → HCID 86704363, Verbindung

HRID 573535

Reaktionsgleichung

Reaktionsgleichung von HRID 573535
CO.[CH:3]([C@@H:5]1[C@@H:14]2[C@@H:8]([O:9][CH2:10][C@@H:11]([CH2:15][CH2:16][CH2:17][C:18]([O:20][CH:21](C)C)=[O:19])[CH2:12][CH2:13]2)[CH2:7][C@H:6]1[O:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][O:26]1)=O.[C:31](=O)([O-])[O-].[K+].[K+].C/C(/[O-])=C(/P(OC)(OC)=O)\[N+]#N>C(OCC)(=O)C>[C:3]([C@@H:5]1[C@@H:14]2[C@@H:8]([O:9][CH2:10][C@@H:11]([CH2:15][CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH2:12][CH2:13]2)[CH2:7][C@H:6]1[O:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][O:26]1)#[CH:31]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 11430Potassium Carbonate2×HCID 866653202-Propanyl 4-[(3S,5aR,6R,7R,8aS)-6-formyl-7-(tetrahydro-2H-pyran-2-yloxy)octahydro-2H-cyclopenta[b]oxepin-3-yl]butanoateHCID 178502985HCID 178502985, Verbindung2×

Produkt 1

HCID 86704363HCID 86704363, VerbindungAusbeute 28,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a methanol solution (2.3 mL) of the compound (180 mg) produced in Example 13, potassium carbonate (94 mg) and a Bestmann reagent (dimethyl-1-diazo-2-oxopropyl phosphonate) (105 mg) were added, followed by stirring at room temperature for 6 hours. Further, potassium carbonate (47 mg) and the Bestmann reagent (53 mg) were added, followed by stirring at room temperature overnight. The reaction mixture was cooled to 0° C.; diluted with ethyl acetate; and then separated by adding water. The organic layer was washed with water and a saturated saline; dried with magnesium sulfate; then filtered; and concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=97:3→65:35) to obtain a titled compound (47 mg) having the following physical property values.

Aufarbeitung

  1. stirringby stirring at room temperature overnight
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. customand then separated
  4. additionby adding water
  5. washThe organic layer was washed with water
  6. dry with materialdried with magnesium sulfate
  7. filtrationthen filtered
  8. concentrationand concentrated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=97:3→65:35)

Quellen und Nachweise

ORD-Eintrag
ord-441e73aeea2a42b6aedb923002fc8850
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029574B2

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