Hydrochloric Acid → HCID 14695734, compound

HRID 2231998Notes

Reaction equation

HRID 2231998 reaction equation
[BH4-].[Na+].[C:3]([O:6][C@:7]1([C@:27]2([CH3:28])[C@H:13]([C@H:14]3[C@H:24]([CH2:25][CH2:26]2)[C@:22]2([CH3:23])[C:17](=[CH:18][C:19](=[O:30])[O:20][CH:21]2O)[C@H:16]([Cl:31])[C@H:15]3[OH:32])[CH2:12][CH2:11]1)[C:8](=[O:10])[CH3:9])(=[O:5])[CH3:4].C(=O)([O-])O.[Na+].Cl>O.CO.O1CCCC1>[C:3]([O:6][C@:7]1([C@:27]2([CH3:28])[C@H:13]([C@H:14]3[C@H:24]([CH2:25][CH2:26]2)[C@:22]2([CH3:23])[C:17](=[CH:18][C:19](=[O:30])[O:20][CH2:21]2)[C@H:16]([Cl:31])[C@H:15]3[OH:32])[CH2:12][CH2:11]1)[C:8](=[O:10])[CH3:9])(=[O:5])[CH3:4]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 70357407HCID 70357407, compound

Product 1

HCID 14695734HCID 14695734, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (64 mg) was added to a mixture of 170 mg of 17α-acetoxy-6β-chloro-1ξ,7α-dihydroxy-2-oxa-4-pregnene-3,20-dione, 62 mg of sodium hydrogen carbonate, 4 ml of tetrahydrofuran, 9.2 ml of methanol and 8.2 ml of water. The reaction mixture was stirred at room temperature for 30 minutes, and 4 ml of 50% hydrochloric acid was added. The mixture was extracted with ethyl acetate, and the extract was washed with a saturated aqueous solution of sodium hydrogen carbonate and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was purified by TLC [developing solvent: chloroform/acetone (9/1)] to give 154 mg of 17α-acetoxy-6β-chloro-7α-hydroxy-2-oxa-4-pregnene-3,20-dione. The 1H NMR spectrum of this compound was the same as that of the compound produced in Example 18.

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
  5. customthe crude product was purified by TLC [developing solvent: chloroform/acetone (9/1)]

Sources & evidence

ORD record
ord-8c45d8e1201241d8b712439ad76cdbc5
Source dataset
uspto-grants-1988_11
Patent number
US04785103

Reaction notes

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