Urea → HCID 86733282, compound

HRID 1606339Notes

Reaction equation

HRID 1606339 reaction equation
[FH:1].NC(N)=O.[O:6]1[C@H:8]2[CH2:9][C@H:10]3[C@:25]([CH3:27])([CH2:26][C@@H:7]12)[C@@H:24]1[C@H:13]([C@H:14]2[C@:21]([CH3:29])([CH2:22][C:23]1=[O:28])[C@@H:17]([C:18](=[O:20])[CH3:19])[CH2:16][CH2:15]2)[CH2:12][CH2:11]3>C(=O)(O)[O-].[Na+]>[F:1][C@H:7]1[CH2:26][C@@:25]2([CH3:27])[C@@H:10]([CH2:11][CH2:12][C@@H:13]3[C@@H:24]2[C:23](=[O:28])[CH2:22][C@@:21]2([CH3:29])[C@H:14]3[CH2:15][CH2:16][C@@H:17]2[C:18](=[O:20])[CH3:19])[CH2:9][C@@H:8]1[OH:6]

Participants

5

Reactant 3

HCID 1176UreaHCID 14917Hydrofluoric AcidHCID 86733130HCID 86733130, compound

Product 1

HCID 86733282HCID 86733282, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

Anhydrous hydrofluoric acid (50 ml.) was added slowly to urea (40 g.) to give a colourless liquid. To 11 ml. of the liquid was added 2α,3α-epoxy-5α-pregnane-11,20-dione (650 mg.), and the clear solution was stirred at room temperature overnight. It was poured into saturated sodium bicarbonate solution (250 ml), and the white precipitate was extracted into chloroform. The organic solution was washed with water, dried over sodium sulphate and evaporated to give a white foam (565 mg.). Recrystallisation from acetonepetrol gave the title compound m.p. 174°-178°, [α]D α+114°.

Workup

  1. customto give a colourless liquid
  2. extractionthe white precipitate was extracted into chloroform
  3. washThe organic solution was washed with water
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customto give a white foam (565 mg.)
  7. customRecrystallisation from acetonepetrol

Sources & evidence

ORD record
ord-440fbc7b76784259b69be753410f90f5
Source dataset
uspto-grants-1976_04
Patent number
US03952031

Reaction notes

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