Water → HCID 86733303, compound

HRID 1606367Notes

Reaction equation

HRID 1606367 reaction equation
[O:1]1[C@H:3]2[CH2:4][C@H:5]3[C@:20]([CH3:22])([CH2:21][C@@H:2]12)[C@@H:19]1[C@H:8]([C@H:9]2[C@:16]([CH3:24])([CH2:17][C:18]1=[O:23])[C@@H:12]([C:13](=[O:15])[CH3:14])[CH2:11][CH2:10]2)[CH2:7][CH2:6]3.[N-:25]=[N+:26]=[N-:27].[Na+].O>CS(C)=O.S(=O)(=O)(O)O>[N:25]([C@H:2]1[CH2:21][C@@:20]2([CH3:22])[C@@H:5]([CH2:6][CH2:7][C@@H:8]3[C@@H:19]2[C:18](=[O:23])[CH2:17][C@@:16]2([CH3:24])[C@H:9]3[CH2:10][CH2:11][C@@H:12]2[C:13](=[O:15])[CH3:14])[CH2:4][C@@H:3]1[OH:1])=[N+:26]=[N-:27]

Participants

6

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 86733130HCID 86733130, compound

Product 1

HCID 86733303HCID 86733303, compoundYield 51.3%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

2α,3α-Epoxy-5α-pregnane-11,20-dione (500 mg) was dissolved in dimethylsulphoxide (25 ml) and sodium azide (1.5 g) added to the solution. Concentrated sulphuric acid (10 drops) was added and the mixture heated on a steam bath for 48 hours. The solution was poured into iced water (600 ml) and the precipitate extracted into ether (100 ml). The ether extract was washed with water (4 + 250 ml) and then saturated sodium bicarbonate solution (250 ml) and finally water (250 ml.). The organic solution was dried over anhydrous sodium sulphate and evaporated to a white foam which was purified by preparative T.L.C. using ethyl acetate/petrol (1/1) run twice. The main band gave title compound (290 mg;) as a foam, [α]D + 95° (c, 0.98).

Workup

  1. temperaturethe mixture heated on a steam bath for 48 hours
  2. extractionthe precipitate extracted into ether (100 ml)
  3. extractionThe ether extract
  4. washwas washed with water (4 + 250 ml)
  5. dry with materialThe organic solution was dried over anhydrous sodium sulphate
  6. customevaporated to a white foam which
  7. customwas purified by preparative T.L.C

Sources & evidence

ORD record
ord-85f597b4f4a34357ae31c4792cf626de
Source dataset
uspto-grants-1976_04
Patent number
US03952031

Reaction notes

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