反应 #92999

ord-8ad86bbd00414540bc192105b311a358

反应方程式

O=S(=O)(O)O
sulfuric acid
CC[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]2(C)[C@H]1OC(=O)CO
16β-ethyl-17β-glycoloyloxy-4-estren-3-one
O=C1CCCC(=O)O1
glutaric anhydride
CCN(CC)CC
triethylamine
→
CC[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]2(C)[C@H]1OC(=O)COC(=O)CCCC(=O)O
above-identified compound
收率 56.2%
CC[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]2(C)[C@H]1OC(=O)COC(=O)CCCC(=O)O
16β-Ethyl-17β-(3-carboxypropyl)carbonyloxyacetoxy-4-estren-3-one
收率 56.2%

反应物

O=S(=O)(O)O
sulfuric acid
CC[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]2(C)[C@H]1OC(=O)CO
16β-ethyl-17β-glycoloyloxy-4-estren-3-one
O=C1CCCC(=O)O1
glutaric anhydride
CCN(CC)CC
triethylamine

试剂

无

溶剂

CN(C)C=O
dimethylformamide

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    其他to stand at room temperature
  2. 2
    其他(15°-25° C.)
  3. 3
    其他for 3 hours
  4. 4
    萃取followed by extraction with 100 ml of ethyl acetate
  5. 5
    其他The organic layer is separated
  6. 6
    洗涤washed with water and saturated aqueous sodium chloride solution
  7. 7
    干燥dried over anhydrous magnesium sulfate
  8. 8
    workup.DISTILLATIONThe solvent is then distilled off under reduced pressure
  9. 9
    洗涤the residue is subjected to column chromatography, elution
  10. 10
    其他The eluate is evaporated under reduced pressure
  11. 11
    其他to remove the solvent
  12. 12
    其他giving a colorless oil, which

实验过程

In 10 ml of dimethylformamide is dissolved 0.5 g of 16β-ethyl-17β-glycoloyloxy-4-estren-3-one, and 0.2 g of glutaric anhydride and then 0.3 ml of triethylamine are added to the above solution. The mixture is allowed to stand at room temperature (15°-25° C.) for 3 hours and poured into 20 ml of 10% aqueous sulfuric acid, followed by extraction with 100 ml of ethyl acetate. The organic layer is separated, 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 200 ml of ethyl acetate. The eluate is evaporated under reduced pressure to remove the solvent, giving a colorless oil, which is allowed to stand to give 0.37 g of the above-identified compound as a solid.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US04609650uspto-grants-1986_09