Water → 16beta-Ethyl-17beta-pivaloyloxyacetoxy-4-estren-3-one

HRID 64720

Reaktionsgleichung

Reaktionsgleichung von HRID 64720
[C:1]([OH:7])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[OH-].[Na+].O.[CH2:11]([C@H:13]1[CH2:18][C@H:17]2[C@H:19]3[C@H:28]([CH2:29][CH2:30][C@:15]2([CH3:16])[C@H:14]1[O:32][C:33](=[O:36])[CH2:34]Br)[C@@H:27]1[C:22](=[CH:23][C:24](=[O:31])[CH2:25][CH2:26]1)[CH2:21][CH2:20]3)[CH3:12]>CC(C)=O.C(OCC)(=O)C.CN(C=O)C>[CH2:11]([C@H:13]1[CH2:18][C@H:17]2[C@H:19]3[C@H:28]([CH2:29][CH2:30][C@:15]2([CH3:16])[C@H:14]1[O:32][C:33](=[O:36])[CH2:34][O:6][C:1](=[O:7])[C:2]([CH3:5])([CH3:4])[CH3:3])[C@@H:27]1[C:22](=[CH:23][C:24](=[O:31])[CH2:25][CH2:26]1)[CH2:21][CH2:20]3)[CH3:12]

Komponenten

8

Edukt 4

HCID 962WaterHCID 6417Pivalic acidHCID 14798Sodium HydroxideHCID 1559376416beta-Ethyl-17beta-bromoacetoxy-4-estren-3-one

Produkt 1

HCID 7046739316beta-Ethyl-17beta-pivaloyloxyacetoxy-4-estren-3-oneAusbeute 87,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 180AcetoneLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In 20 ml of acetone is dissolved 0.61 g of pivalic acid, and 3.0 ml of 2N-NaOH and 10 ml of water are added. And then, 1.2 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one and 30 ml of DMF are added and the mixture is refluxed for 6 hours. After cooling, 150 ml of ethyl acetate is added and the organic layer is separated. The aqueous layer is is further extracted with 50 ml of ethyl acetate. The organic layers are combined, washed with water and saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent is then distilled off under reduced pressure and the residue is subjected to column chromatography, elution being carried out with 400 ml of diisopropyl ether. The eluate is evaporated under reduced pressure to remove the solvent, giving 1.1 g of the above-identified compound as a colorless viscous oil.

Aufarbeitung

  1. additionare added
  2. temperaturethe mixture is refluxed for 6 hours
  3. temperatureAfter cooling
  4. customthe organic layer is separated
  5. extractionThe aqueous layer is is further extracted with 50 ml of ethyl acetate
  6. washwashed with water and saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent is then distilled off under reduced pressure
  9. washthe residue is subjected to column chromatography, elution
  10. customThe eluate is evaporated under reduced pressure
  11. customto remove the solvent

Quellen und Nachweise

ORD-Eintrag
ord-e7605e3a96a64f4e8089c5273357f85c
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04609650

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