Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Methanol | HCID 887 | — |
| Edukt | Potassium Carbonate | HCID 11430 | — |
| Edukt | 2-Propanyl 4-[(3S,5aR,6R,7R,8aS)-6-formyl-7-(tetrahydro-2H-pyran-2-yloxy)octahydro-2H-cyclopenta[b]oxepin-3-yl]butanoate | HCID 86665320 | — |
| Edukt | HCID 178502985 | HCID 178502985 | — |
| Lösungsmittel | Ethyl Acetate | HCID 8857 | — |
| Produkt | HCID 86704363 | HCID 86704363 | 28,4% |
Reaktionsschritte
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.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US09029574B2 |
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| Quelldatensatz | uspto-grants-2015_05 |
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| ORD ID | ord-441e73aeea2a42b6aedb923002fc8850 |
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| Quellennotiz | uspto-grants-2015_05 |
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