反応 #93015

反応方程式

N-t-butoxycarbonylglycine

potassium t-butoxide

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

→

above-identified compound

収率 89.2%

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

収率 89.2%

溶媒

acetone

water

反応条件

後処理

1. 1
   workup.ADDITIONis added to the solution
2. 2
   温度The mixture is refluxed for 12 hours
3. 3
   workup.DISTILLATIONThe solvent is then distilled off under reduced pressure
4. 4
   抽出the residue is extracted with 150 ml of ethyl acetate
5. 5
   洗浄The organic layer is washed with water and saturated aqueous sodium chloride solution
6. 6
   乾燥dried 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
   その他chromatographed on a silica gel column
10. 10
    洗浄passage of 100 ml of diisopropyl ether, elution
11. 11
    その他The eluate is evaporated under reduced pressure
12. 12
    その他to remove the solvent

実験手順

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.

出典