Citric Acid → 3alpha-Hydroxy-21-morpholino-5alpha-pregnane-11,20-dione citrate

HRID 1576782Notes

Reaction equation

HRID 1576782 reaction equation
[OH:1][C@@H:2]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:24]2[C:23](=[O:29])[CH2:22][C@@:21]2([CH3:30])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:20])[CH2:13][N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH2:3]1.[C:31]([OH:43])(=[O:42])[CH2:32][C:33]([CH2:38][C:39]([OH:41])=[O:40])([C:35]([OH:37])=[O:36])[OH:34]>C(O)C>[C:31]([OH:43])(=[O:42])[CH2:32][C:33]([CH2:38][C:39]([OH:41])=[O:40])([C:35]([OH:37])=[O:36])[OH:34].[OH:1][C@@H:2]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:24]2[C:23](=[O:29])[CH2:22][C@@:21]2([CH3:30])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:20])[CH2:13][N:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)[CH2:3]1

Participants

4

Reactant 2

HCID 311Citric AcidHCID 867340213alpha-Hydroxy-21-morpholino-5alpha-pregnane-11,20-dione

Product 1

HCID 867340303alpha-Hydroxy-21-morpholino-5alpha-pregnane-11,20-dione citrate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3α-hydroxy-21-morpholino-5α-pregnane-11,20-dione (83.52 mg. 0.2 mmole) in absolute ethanol (1 ml.) was treated with 0.1M aqueous citric acid (2 ml. 0.2 mmole). The ethanol was removed by evaporation and the resulting solution freeze-dried. Water (5 ml.) was added, and the cloudy solution obtained left to stand at room temperature for two hours. The solution was filtered through a No. 3 sinter. The flask was rinsed with water (0.5 ml.) and this was also filtered. The sinter and flask were washed with chloroform (10 ml.). The chloroform was washed with saturated sodium bicarbonate solution (2 × 5 ml.) and with water (3 × 5 ml.) and evaporated to a residue which was dried by azeotroping with benzene (6 × 10 ml.) and in vacuo (20.6 mg.). The filtrate waas diluted with water (1 ml.) to give title compound as a 10 mg./ml. aqueous solution with respect to steroid. The pH of the solution was 3.45.

Workup

  1. customThe ethanol was removed by evaporation
  2. customthe resulting solution freeze-dried
  3. additionWater (5 ml.) was added
  4. customthe cloudy solution obtained
  5. waitleft
  6. filtrationThe solution was filtered through a No
  7. washThe flask was rinsed with water (0.5 ml.)
  8. filtrationthis was also filtered
  9. washThe sinter and flask were washed with chloroform (10 ml.)
  10. washThe chloroform was washed with saturated sodium bicarbonate solution (2 × 5 ml.) and with water (3 × 5 ml.)
  11. customevaporated to a residue which
  12. customwas dried
  13. customby azeotroping with benzene (6 × 10 ml.) and in vacuo (20.6 mg.)
  14. additionThe filtrate waas diluted with water (1 ml.)

Sources & evidence

ORD record
ord-0abf1b47234441239fad800cd50ef588
Source dataset
uspto-grants-1976_09
Patent number
US03983111

Reaction notes

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