Hydrochloric Acid → HCID 54482952, compound

HRID 1607975Notes

Reaction equation

HRID 1607975 reaction equation
[OH:1][C@@H:2]1[C@@:21]2([CH3:22])[C@@H:14]([CH2:15][CH2:16][C@@H:17]2[C:18](=[O:20])[CH3:19])[C@H:13]2[C@@H:4]([C@:5]3([CH3:24])[C:10]([CH2:11][CH2:12]2)=[CH:9][C:8](=[O:23])[CH:7]=[CH:6]3)[CH2:3]1.[CH3:25][S:26](Cl)(=[O:28])=[O:27].Cl>N1C=CC=CC=1>[S:26]([O:1][C@@H:2]1[C@@:21]2([CH3:22])[C@@H:14]([CH2:15][CH2:16][C@@H:17]2[C:18](=[O:20])[CH3:19])[C@H:13]2[C@@H:4]([C@:5]3([CH3:24])[C:10]([CH2:11][CH2:12]2)=[CH:9][C:8](=[O:23])[CH:7]=[CH:6]3)[CH2:3]1)([CH3:25])(=[O:28])=[O:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 53997316HCID 53997316, compound

Product 1

HCID 54482952HCID 54482952, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

12α-Hydroxypregna-1,4-diene-3,20-dione (3.3 g) was dissolved in 17 mlof pyridine. To the solution was added 3.4 g of methanesulfonyl chloride, and the mixture was stirred at room temperature for 8 hours. The reaction mixture was then poured into 300 ml of diluted hydrochloric acid, and the resulting mixture was extracted with three 300 ml portions of benzene. Theextracts were combined and washed in sequence with diluted hydrochloric acid, aqueous sodium bicarbonate solution and water, and dried over anhydrous magnesium sulfate. Low-boiling fractions were distilled off under reduced pressure from the extract to give 3.8 g of crude 12α-mesyloxypregna-1,4-diene-3,20-dione, which was recrystallized from ethyl acetate. The physical properties for the thus-purified product were as follows:

Workup

  1. extractionthe resulting mixture was extracted with three 300 ml portions of benzene
  2. washwashed in sequence with diluted hydrochloric acid, aqueous sodium bicarbonate solution and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationwere distilled off under reduced pressure from the
  5. extractionextract

Sources & evidence

ORD record
ord-cf303ea9fbf046edba53a295be60087c
Source dataset
uspto-grants-1989_09
Patent number
US04867914

Reaction notes

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