2-Methylbutanoic Acid → 16beta-Ethyl-17beta-(2-methylbutyryl)oxyacetoxy-4-estren-3-one

HRID 64725

반응식

HRID 64725 반응식
[CH2:1]([C@H:3]1[CH2:8][C@H:7]2[C@H:9]3[C@H:18]([CH2:19][CH2:20][C@:5]2([CH3:6])[C@H:4]1[O:22][C:23](=[O:26])[CH2:24]Br)[C@@H:17]1[C:12](=[CH:13][C:14](=[O:21])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3)[CH3:2].C(OCC)(=O)C.[CH3:33][CH:34]([CH2:38][CH3:39])[C:35]([OH:37])=[O:36]>CC(C)=O.[OH-].[Na+].O>[CH2:1]([C@H:3]1[CH2:8][C@H:7]2[C@H:9]3[C@H:18]([CH2:19][CH2:20][C@:5]2([CH3:6])[C@H:4]1[O:22][C:23](=[O:26])[CH2:24][O:37][C:35](=[O:36])[CH:34]([CH3:33])[CH2:38][CH3:39])[C@@H:17]1[C:12](=[CH:13][C:14](=[O:21])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3)[CH3:2]

참가 물질

7

반응물 3

HCID 83142-Methylbutanoic AcidHCID 8857Ethyl AcetateHCID 1559376416beta-Ethyl-17beta-bromoacetoxy-4-estren-3-one

생성물 1

HCID 7046791616beta-Ethyl-17beta-(2-methylbutyryl)oxyacetoxy-4-estren-3-one

시약·촉매·용매 3

HCID 180Acetone용매HCID 962Water용매HCID 14798Sodium Hydroxide용매

실험 절차

In 30 ml of acetone is dissolved 0.4 ml of 2-methylbutyric acid, and 2.0 ml of 2N-NaOH and 3 ml of water is added, followed by addition of 0.88 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one. The mixture is refluxed for 6 hours and allowed to stand at room temperature (15°-25° C.) for 2 days, followed by addition of 150 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. Following passage of 100 ml of diisopropyl ether-n-hexane (2:8), elution is carried out with 400 ml of a 1:1 mixture of the same solvents. The eluate is evaporated under reduced pressure to remove the solvent, giving 0.8 g of the above-identified compound as a light-yellow viscous oil.

후처리

  1. additionis added
  2. temperatureThe mixture is refluxed for 6 hours
  3. customto stand at room temperature
  4. custom(15°-25° C.)
  5. customfor 2 days
  6. customThe organic layer is separated
  7. washwashed with water and saturated aqueous sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationThe solvent is then distilled off under reduced pressure
  10. washpassage of 100 ml of diisopropyl ether-n-hexane (2:8), elution
  11. additionis carried out with 400 ml of a 1:1 mixture of the same solvents
  12. customThe eluate is evaporated under reduced pressure
  13. customto remove the solvent

출처 및 근거

ORD 기록
ord-361e017f28494fbb8b46ffc7156fc566
출처 데이터셋
uspto-grants-1986_09
특허 번호
US04609650

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