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

HRID 1576787Notes

Reaction equation

HRID 1576787 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].[OH-].[Na+]>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

5

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 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

3α-Hydroxy-21-morpholino-5α-pregnane-11,20-dione (500 mg) in ethanol (60 ml) was treated with N/10 aqueous citric acid (12 ml) and the mixture was evaporated to dryness. The residue was dried in vacuo to constant weight and the resultant solid dissolved in water (30 ml). The solution was filtered and the solid collected (1 mg) and discarded. Water was added to the filtrate until a concentration of 10 mg/ml with respect to steroid was obtained. The pH of this solution was 3.4. 2N-Aqueous sodium hydroxide was added dropwise until a pH of 4.7 was achieved.

Workup

  1. customthe mixture was evaporated to dryness
  2. customThe residue was dried in vacuo to constant weight
  3. dissolutionthe resultant solid dissolved in water (30 ml)
  4. filtrationThe solution was filtered
  5. customthe solid collected (1 mg)
  6. additionWater was added to the filtrate until a concentration of 10 mg/ml with respect to steroid
  7. customwas obtained

Sources & evidence

ORD record
ord-f7bdab134cfe479a93c1d7f11f0848f2
Source dataset
uspto-grants-1976_09
Patent number
US03983111

Reaction notes

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