Phosphate → HCID 70460175, compound

HRID 1285318Notes

Reaction equation

HRID 1285318 reaction equation
S(=O)(=O)(O)O.[C:6]([C@:8]1([OH:30])[C:13](=[CH2:14])[CH2:12][C@H:11]2[C@H:15]3[C@H:25]([CH2:26][CH2:27][C@:9]12[CH3:10])[C@:23]1([CH3:24])[C:18](=[CH:19][C:20](=[O:28])[CH2:21][CH2:22]1)[C:17]([CH3:29])=[CH:16]3)#[CH:7].P([O-])([O-])([O-])=[O:32]>O.CO.C1COCC1>[C:6]([C@:8]1([OH:30])[C:13](=[CH2:14])[CH2:12][C@H:11]2[C@H:15]3[C@H:25]([CH2:26][CH2:27][C@:9]12[CH3:10])[C@:23]1([CH3:24])[C:18](=[CH:19][C:20](=[O:28])[CH2:21][CH2:22]1)[C:17]([CH3:29])=[CH:16]3)(=[O:32])[CH3:7]

Participants

7

Reactant 3

HCID 1061PhosphateHCID 1118Sulfuric AcidHCID 86740640HCID 86740640, compound

Product 1

HCID 70460175HCID 70460175, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Mercuric oxide (83 mg) dissolved in water (18 ml) containing sulfuric acid (0.11 ml) was added to 17α-ethynyl-17β-hydroxy-6-methyl-16-methyleneandrosta-4,6-diene-3-one (IVA, Example 20, 1.30 g) dissolved in a methanol (19 ml)-THF (3.8 ml) mixture. The mixture was heated at 40° (bath temperature) for 6 hr and then permitted to sit at 20°-25° overnight. Celite (1.7 g) and phosphate buffer (2 ml) were added, the mixture stirred and filtered. The solids were washed with methanol and THF. The filtrate was concentrated under reduced pressure until solids dropped out. Methanol was added and the mixture heated, seeded. The mixture was concentrated under reduced pressure, methylene chloride was added, the mixture was washed with buffer, dried over sodium sulfate, filtered. The filtrate was concentrated under reduced pressure to give the title compound.

Workup

  1. temperatureThe mixture was heated at 40° (bath temperature) for 6 hr
  2. filtrationfiltered
  3. washThe solids were washed with methanol and THF
  4. concentrationThe filtrate was concentrated under reduced pressure until solids
  5. additiondropped out
  6. additionMethanol was added
  7. temperaturethe mixture heated
  8. concentrationThe mixture was concentrated under reduced pressure, methylene chloride
  9. additionwas added
  10. washthe mixture was washed with buffer,
  11. dry with materialdried over sodium sulfate
  12. filtrationfiltered
  13. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5ae3dfdadddd4bcd9ec280bfc1440fde
Source dataset
uspto-grants-1986_01
Patent number
US04567001

Reaction notes

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