Sodium potassium tartrate tetrahydrate → Progesterone Impurity D

HRID 1069053Notes

Reaction equation

HRID 1069053 reaction equation
[C:1]([O:4][C@H:5]([C@@H:7]1[C@:24]2([CH3:25])[C@H:10]([C@H:11]3[C@H:21]([CH2:22][CH2:23]2)[C@:19]2([CH3:20])[C:14]([CH2:15][C@@H:16]([OH:26])[CH2:17][CH2:18]2)=[CH:13][CH2:12]3)[CH2:9][CH2:8]1)[CH3:6])(=[O:3])[CH3:2].O.O.O.O.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1.CC(=O)CC.O>[C:1]([O:4][C@H:5]([C@@H:7]1[C@:24]2([CH3:25])[C@H:10]([C@H:11]3[C@H:21]([CH2:22][CH2:23]2)[C@:19]2([CH3:20])[C:14](=[CH:15][C:16](=[O:26])[CH2:17][CH2:18]2)[CH2:13][CH2:12]3)[CH2:9][CH2:8]1)[CH3:6])(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 2724148Sodium potassium tartrate tetrahydrateHCID 21969303(3beta,20S)-pregn-5-ene-3,20-diol 20-acetate

Product 1

HCID 57099835Progesterone Impurity DYield 82.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

—Aluminium isopropoxide (18.1 g) was added to a solution of (3β,20S)-pregn-5-ene-3,20-diol 20-acetate (21.9 g) in dry toluene (252 ml) and dry 2-butanone (156 ml). The mixture was heated under reflux for 2 hours, then cooled, whereupon a solution of potassium sodium tartrate tetrahydrate (91.4 g) in water (90 ml) was added. The mixture was stirred for 30 min. and filtered. The filtrate was poured into brine and the product extracted into ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. Column chromatography afforded (20S)-20-(acetyloxy)pregn-4-en-3-one (compound 6a; 17.9 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. additionwas added
  4. filtrationfiltered
  5. additionThe filtrate was poured into brine
  6. extractionthe product extracted into ethyl acetate
  7. washThe combined organic phases were washed with brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-32b00294679a41949c7d5522c48bd113
Source dataset
uspto-grants-2001_06
Patent number
US06251887B1

Reaction notes

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