Dimethylformamide → 16beta-Ethyl-17beta-(3,3-dimethylbutyryl)oxyacetoxy-4-estren-3-one

HRID 64733

Reaktionsgleichung

Reaktionsgleichung von HRID 64733
[CH3:1][C:2]([CH3:8])([CH3:7])[CH2:3][C:4]([OH:6])=[O:5].[OH-].[Na+].[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].CN(C=O)C>CC(C)=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][O:5][C:4](=[O:6])[CH2:3][C:2]([CH3:8])([CH3:7])[CH3:1])[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

6

Edukt 4

HCID 6228DimethylformamideHCID 14057tert-Butylacetic acidHCID 14798Sodium HydroxideHCID 1559376416beta-Ethyl-17beta-bromoacetoxy-4-estren-3-one

Produkt 1

HCID 7046727216beta-Ethyl-17beta-(3,3-dimethylbutyryl)oxyacetoxy-4-estren-3-oneAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

In 10 ml of acetone is dissolved 1.16 g of 3,3-dimethylbutyric acid, and 5.0 ml of 2N-NaOH is added, followed by addition of 1.15 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one and 20 ml of DMF. The mixture is refluxed for 5 hours, and thereafter treated in the same manner as Example 26. The reaction mixture is chromatographed on a silica gel column. Following passage of 200 ml of n-hexanediisopropyl ether (3:7), elution is carried out with a 1:1 mixture of the same solvents. The eluate is evaporated under reduced pressure to remove the solvent, giving 0.76 g of the above-identified compound as a colorless viscous oil.

Aufarbeitung

  1. additionis added
  2. temperatureThe mixture is refluxed for 5 hours
  3. additiontreated in the same manner as Example 26
  4. customThe reaction mixture is chromatographed on a silica gel column
  5. washpassage of 200 ml of n-hexanediisopropyl ether (3:7), elution
  6. additionis carried out with a 1:1 mixture of the same solvents
  7. customThe eluate is evaporated under reduced pressure
  8. customto remove the solvent

Quellen und Nachweise

ORD-Eintrag
ord-fc603816905c42dc89c27894771d8e96
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04609650

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