Water → HCID 68748821, Verbindung

HRID 573532Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 573532
[CH3:1][Si](C)(C)N[Si](C)(C)C.[K].[C:11]1(C)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH:18]([C@@H:20]1[C@@H:29]2[C@@H:23]([O:24][CH2:25][C@@H:26]([CH2:30][CH2:31][CH2:32][C:33]([O:35][CH:36]([CH3:38])[CH3:37])=[O:34])[CH2:27][CH2:28]2)[CH2:22][C@H:21]1[O:39][CH:40]1[CH2:45][CH2:44][CH2:43][CH2:42][O:41]1)=O.O.C([O:50][CH2:51][CH3:52])(=O)C>COCCOC>[O:50]([CH2:51][CH2:52]/[CH:1]=[CH:18]/[C@@H:20]1[C@@H:29]2[C@@H:23]([O:24][CH2:25][C@@H:26]([CH2:30][CH2:31][CH2:32][C:33]([O:35][CH:36]([CH3:38])[CH3:37])=[O:34])[CH2:27][CH2:28]2)[CH2:22][C@H:21]1[O:39][CH:40]1[CH2:45][CH2:44][CH2:43][CH2:42][O:41]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 866653202-Propanyl 4-[(3S,5aR,6R,7R,8aS)-6-formyl-7-(tetrahydro-2H-pyran-2-yloxy)octahydro-2H-cyclopenta[b]oxepin-3-yl]butanoateHCID 131731101HCID 131731101, Verbindung

Produkt 1

HCID 68748821HCID 68748821, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Under the argon atmosphere, the compound (165 mg) produced in Example 100 was dissolved in DME (2 mL), the solution was cooled to −78° C., followed by addition of a 0.5M potassium hexamethyldisilazane/toluene solution (0.90 mL). After stirring the mixture at −78° C. for 20 minutes, a DME (1.5 mL) solution of the compound produced in Example 13 was added dropwise, and stirring at the same temperature was carried out for 10 minutes. After raising a temperature of the reaction solution to 0° C., water was added, and the extract obtained by extraction with ethyl acetate was washed with water and a saturated saline; dried with anhydrous magnesium sulfate; and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10→65:35) to obtain a titled compound (177 mg) having the following physical property values.

Aufarbeitung

  1. stirringstirring at the same temperature
  2. waitwas carried out for 10 minutes
  3. temperatureAfter raising a temperature of the reaction solution to 0° C.
  4. washwas washed with water
  5. dry with materialdried with anhydrous magnesium sulfate
  6. concentrationand concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10→65:35)

Quellen und Nachweise

ORD-Eintrag
ord-b2c2da4a66d94051b2baa9799b389246
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029574B2

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