Hydrochloric Acid → HCID 70166578, compound

HRID 566889Notes

Reaction equation

HRID 566889 reaction equation
[C:1]([O:9][C@H:10]1[CH2:37][CH2:36][C@@:35]2([CH3:38])[C:12](=[CH:13][CH:14]=[C:15]3[C@@H:34]2[CH2:33][CH2:32][C@@:31]2([CH3:39])[C@H:16]3[CH2:17][CH2:18][C@@H:19]2[C@H:20]([CH3:30])[CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[C:11]1([CH3:41])[CH3:40])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC(=O)C)(=O)C.Cl.[OH-].[NH4+]>C(Cl)(Cl)Cl>[C:1]([O:9][C@H:10]1[CH2:37][CH2:36][C@@:35]2([CH3:38])[C@@H:12]([CH:13]=[CH:14][C:15]3[C@@H:34]2[CH2:33][CH2:32][C@@:31]2([CH3:39])[C:16]=3[CH2:17][CH2:18][C@@H:19]2[C@H:20]([CH3:30])[CH2:21][O:22][Si:23]([C:26]([CH3:28])([CH3:29])[CH3:27])([CH3:25])[CH3:24])[C:11]1([CH3:40])[CH3:41])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 14923Ammonium HydroxideHCID 70167450HCID 70167450, compound2×

Product 1

HCID 70166578HCID 70166578, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

—Hydrogen chloride gas was passed into a solution of (3β,20S)-21-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4,4,20-trimethylpregna-5,7-dien-3-ol benzoate (compound 8; Example 1, step vi; 25.0 g) and acetic anhydride (40 ml) in chloroform (250 ml) for 30 min. The mixture was heated at reflux temperature for 50 min.; addition of hydrogen chloride gas was continued for the first 20 min. After cooling to 0° C., an aqueous solution of ammonium hydroxide (5%) was added, and the mixture was stirred for 1.5 h. The product was extracted into dichloromethane; the combined organic phases were washed with a saturated aqueous solution of sodium hydrogencarbonate and brine, dried over sodium sulfate and concentrated under reduced pressure to give (3β,5α,20S)-21-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4,4,20-trimethylpregna-6,8(14)-dien-3-ol benzoate (24.6 g). The product was used as such in the next step.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for 50 min.
  3. customwas continued for the first 20 min
  4. extractionThe product was extracted into dichloromethane
  5. washthe combined organic phases were washed with a saturated aqueous solution of sodium hydrogencarbonate and brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8c3656b6777348fd8f3baec44e38e63f
Source dataset
uspto-grants-2001_01
Patent number
US06177420B1

Reaction notes

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