Hydrochloric Acid → HCID 70166579, compound

HRID 1385622Notes

Reaction equation

HRID 1385622 reaction equation
[C:1]([O:9][C@H:10]1[CH2:36][CH2:35][C@@:34]2([CH3:37])[C:12](=[CH:13][CH:14]=[C:15]3[C@@H:33]2[CH2:32][CH2:31][C@@:30]2([CH3:38])[C@H:16]3[CH2:17][CH2:18][C@@H:19]2[C@@H:20]([O:22][Si](C(C)(C)C)(C)C)[CH3:21])[C:11]1([CH3:40])[CH3:39])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.Cl.C(=O)([O-])O.[Na+]>C(O)C>[C:1]([O:9][C@H:10]1[CH2:36][CH2:35][C@@:34]2([CH3:37])[C@@H:12]([CH2:13][CH2:14][C:15]3[C:16]4[C@:30]([CH3:38])([CH2:31][CH2:32][C:33]=32)[C@@H:19]([C@@H:20]([OH:22])[CH3:21])[CH2:18][CH:17]=4)[C:11]1([CH3:39])[CH3:40])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:1]([O:9][C@H:10]1[CH2:36][CH2:35][C@@:34]2([CH3:37])[C@@H:12]([CH:13]=[CH:14][C:15]3[C@@H:33]2[CH2:32][CH2:31][C@@:30]2([CH3:38])[C:16]=3[CH2:17][CH2:18][C@@H:19]2[C@@H:20]([OH:22])[CH3:21])[C:11]1([CH3:39])[CH3:40])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 516892Sodium BicarbonateHCID 70167631HCID 70167631, compound

Product 2

HCID 70166579HCID 70166579, compoundHCID 70167600HCID 70167600, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

xii)—A mixture of compound 12 (36.6 g), toluene (91 ml), ethanol (622 ml; 96%) and concentrated hydrochloric acid (91 ml) was heated under reflux for 4 h. The mixture was cooled and poured into a saturated aqueous solution of sodium hydrogen carbonate (1 l). The product was extracted into ethyl acetate, the combined organic phases were washed with a saturated aqueous solution of sodium hydrogen carbonate and with brine, dried over sodium sulfate, and concentrated under reduced pressure. Column chromatography and crystallization afforded (3β,5α,20S)-4,4-dimethylpregna-8,14-diene-3,20-diol 3-benzoate (compound 13; 7.89 g) and (3β,5α,20S)-4,4-dimethylpregna-6,8(14)-diene-3,20-diol 3-benzoate (3.69 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 h
  3. temperatureThe mixture was cooled
  4. extractionThe product was extracted into ethyl acetate
  5. washthe combined organic phases were washed with a saturated aqueous solution of sodium hydrogen carbonate and with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customColumn chromatography and crystallization

Sources & evidence

ORD record
ord-e572e0664a0f49ecb97adf3c289be69a
Source dataset
uspto-grants-2001_07
Patent number
US06262282B1

Reaction notes

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