Reaktion #93015

Reaktionsgleichung

N-t-butoxycarbonylglycine

potassium t-butoxide

16β-ethyl-17β-bromoacetoxy-4-estren-3-one

→

above-identified compound

Ausbeute 89.2%

16β-Ethyl-17β-(N-t-butoxycarbonylglycyloxy)acetoxy-4-estren-3-one

Ausbeute 89.2%

Lösungsmittel

acetone

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONis added to the solution
2. 2
   TemperaturThe mixture is refluxed for 12 hours
3. 3
   workup.DISTILLATIONThe solvent is then distilled off under reduced pressure
4. 4
   Extraktionthe residue is extracted with 150 ml of ethyl acetate
5. 5
   WaschenThe organic layer is washed with water and saturated aqueous sodium chloride solution
6. 6
   Trocknendried over anhydrous magnesium sulfate
7. 7
   workup.DISTILLATIONThe solvent is distilled off
8. 8
   workup.DISSOLUTIONthe residue is dissolved in a small amount of diisopropyl ether-n-hexane (1:1)
9. 9
   Sonstigechromatographed on a silica gel column
10. 10
    Waschenpassage of 100 ml of diisopropyl ether, elution
11. 11
    SonstigeThe eluate is evaporated under reduced pressure
12. 12
    Sonstigeto remove the solvent

Vorschrift

In a mixture of 40 ml of acetone and 8 ml of water is dissolved 0.7 g of N-t-butoxycarbonylglycine, and 0.42 g of potassium t-butoxide is added to the solution. The mixture is stirred, followed by addition of 1.1 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one. The mixture is refluxed for 12 hours. The solvent is then distilled off under reduced pressure and the residue is extracted with 150 ml of ethyl acetate. The organic layer is washed with water and saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent is distilled off and the residue is dissolved in a small amount of diisopropyl ether-n-hexane (1:1) and chromatographed on a silica gel column. Following passage of 100 ml of diisopropyl ether, elution is carried out with 400 ml of ethyl acetate. The eluate is evaporated under reduced pressure to remove the solvent, giving 1.2 g of the above-identified compound as a viscous oil.

Quelle