Water → HCID 86733303, compound

HRID 1606369Notes

Reaction equation

HRID 1606369 reaction equation
[OH:1][C@@H:2]1[C@@H:21](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:20][C@@:19]2([CH3:33])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:18]2[C:17](=[O:34])[CH2:16][C@@:15]2([CH3:35])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:14])[CH3:13])[CH2:3]1.[N-:36]=[N+:37]=[N-:38].[Na+].O>CS(C)=O>[N:36]([C@H:21]1[CH2:20][C@@:19]2([CH3:33])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:18]2[C:17](=[O:34])[CH2:16][C@@:15]2([CH3:35])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:14])[CH3:13])[CH2:3][C@@H:2]1[OH:1])=[N+:37]=[N-:38]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 86733302HCID 86733302, compound

Product 1

HCID 86733303HCID 86733303, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3α-hydroxy-2β-toluene-p-sulphonyloxy-5α-pregnane-11,20-dione (500 mg) was dissolved in dimethylsulphoxide (20 ml) and sodium azide (1.5 g) added to the solution. The mixture was heated on a steam bath for 30 hours, cooled and poured into water. The precipitate formed was filtered off, dissolved in ether and the solution dried over anhydrous sodium sulphate. The dried solution was evaporated to a foam (300 mg) which was purified by preparative T.L.C. using ethyl acetate/petrol (1/1). The main band (Rf 0.2-0.3) giving title compound (200 mg) as a foam, [α]D + 104° (c 0.93), identical with the above compound.

Workup

  1. temperatureThe mixture was heated on a steam bath for 30 hours
  2. temperaturecooled
  3. customThe precipitate formed
  4. filtrationwas filtered off
  5. dissolutiondissolved in ether
  6. dry with materialthe solution dried over anhydrous sodium sulphate
  7. customThe dried solution was evaporated to a foam (300 mg) which
  8. customwas purified by preparative T.L.C

Sources & evidence

ORD record
ord-52668f6222a5414f83af3b33e6b7af3f
Source dataset
uspto-grants-1976_04
Patent number
US03952031

Reaction notes

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