Hydrochloric Acid → HCID 14695734, compound

HRID 2072898Notes

Reaction equation

HRID 2072898 reaction equation
[ClH:1].[C:2]([O:5][C@:6]1([C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16](=[CH:17][C:18](=[O:28])[O:19][CH2:20]2)[C@H:15]2[O:29][C@@H:14]32)[CH2:11][CH2:10]1)[C:7](=[O:9])[CH3:8])(=[O:4])[CH3:3].O>O1CCCC1>[C:2]([O:5][C@:6]1([C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16](=[CH:17][C:18](=[O:28])[O:19][CH2:20]2)[C@H:15]([Cl:1])[C@H:14]3[OH:29])[CH2:11][CH2:10]1)[C:7](=[O:9])[CH3:8])(=[O:4])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 14695738HCID 14695738, compound

Product 1

HCID 14695734HCID 14695734, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Concentrated hydrochloric acid (0.1 ml) was adde*d to a solution of 97 mg of 17α-acetoxy-6α,7α-epoxy-2-oxa-4-pregnene-3,20-dione in 4 ml of tetrahydrofuran, and the solution was stirred at room temperature for 10 minutes. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium hydrogen carbonate, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give 102 mg of 17α-acetoxy-6β-chloro-7α-hydroxy-2-oxa-4-pregnene-3,20-dione.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with a saturated aqueous solution of sodium hydrogen carbonate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7e8f261505774ad2b32c9db8467d3d35
Source dataset
uspto-grants-1990_04
Patent number
US04914106

Reaction notes

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