Acetone → Anecortave Acetate

HRID 65345

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HRID 65345 반응식
[OH:1][C@:2]1([C@:28]2([CH3:29])[C@H:14]([C@H:15]3[C:25](=[CH:26][CH2:27]2)[C@:23]2([CH3:24])[C:18](=[CH:19][C:20](=[O:30])[CH2:21][CH2:22]2)[CH2:17][CH2:16]3)[CH2:13][CH2:12]1)[C:3]([O:5]C1C=CC=CC=1)=[CH2:4].P([O-])([O-])([O-])=O.[K+].[K+].[K+].OOS([O-])=O.[K+].[OH:45]S([O-])(=O)=O.[K+].C[C:52]([CH3:54])=[O:53]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(Cl)Cl>[OH:1][C@:2]1([C@:28]2([CH3:29])[C@H:14]([C@H:15]3[C:25](=[CH:26][CH2:27]2)[C@:23]2([CH3:24])[C:18](=[CH:19][C:20](=[O:30])[CH2:21][CH2:22]2)[CH2:17][CH2:16]3)[CH2:13][CH2:12]1)[C:3](=[O:4])[CH2:5][O:53][C:52](=[O:45])[CH3:54]

참가 물질

9

반응물 5

HCID 180AcetoneHCID 62657Potassium Phosphate, TribasicHCID 516920Potassium bisulfateHCID 1382382517alpha-Hydroxy-20-phenoxypregna-4,9(11),20-trien-3-oneHCID 23707502Potassium hydroxy sulfite

생성물 1

HCID 111332Anecortave Acetate

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 962Water용매HCID 6344Dichloromethane용매

반응 조건

온도
15 °C

실험 절차

17α-hydroxy-20-phenoxypregna-4,9(11),20-trien-3-one (4.05 grams, 10 mmoles) is slurried in a 250 ml round bottom flask, in an aqueous pH 8 potassium phosphate buffer (20 ml, 0.05M in PO4≡) prepared as in Example 1. Tetra n-butylammonium bromide (0.64 grams, 2.0 mmole), acetone (20 ml), methylene chloride (40 ml) are added and the mixture cooled to 15° C. 18.42 grams, 30 mmoles of OXONE® (2KHSO5.KHSO4.K2SO4) is dissolved in 62 ml of water filtered and placed in an addition funnel. The OXONE solution is added dropwise with stirring while maintaining the pH between 6.8 and 7.2 with 30% potassium hydroxide. The reaction is run to completion. Fifty ml of water is added and the reaction mixture is filtered. The filtered solids are rinsed with methylene chloride and water, the layers are separated and the methylene chloride layer is filtered thru a solka flok filter. Two ml of glacial acetic acid are added and the mixture is stirred for 1 hour to yield 2.5 grams of 17α-hydroxy-21 -acetoxy-pregna-4,9(11)-diene-3,20-dione at room temperature.

후처리

  1. filtrationfiltered
  2. customplaced in an addition funnel
  3. additionThe OXONE solution is added dropwise
  4. temperaturewhile maintaining the pH between 6.8 and 7.2 with 30% potassium hydroxide
  5. additionFifty ml of water is added
  6. filtrationthe reaction mixture is filtered
  7. washThe filtered solids are rinsed with methylene chloride and water
  8. customthe layers are separated
  9. filtrationthe methylene chloride layer is filtered
  10. filtrationfilter
  11. additionTwo ml of glacial acetic acid are added
  12. stirringthe mixture is stirred for 1 hour

출처 및 근거

ORD 기록
ord-d1cbf3bc997146c8ba55f3de17402c48
출처 데이터셋
uspto-grants-1986_09
특허 번호
US04613463

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