Hydrochloric Acid → HCID 14695734, compound

HRID 2072900Notes

Reaction equation

HRID 2072900 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% hyrochloric 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-2fdc5105c7954e25b78f7d53cf0551af
Source dataset
uspto-grants-1990_04
Patent number
US04914106

Reaction notes

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