Ammonia → HCID 10427683, compound

HRID 893034Notes

Reaction equation

HRID 893034 reaction equation
[NH3:1].C(O)(=O)C.Cl[C:7]1[C:27](=[O:28])[CH2:26][CH2:25][C@@:24]2([CH3:29])[C:8]=1[CH2:9][CH2:10][C@@H:11]1[C@@H:23]2[CH2:22][CH2:21][C@@:20]2([CH3:30])[C@H:12]1[CH2:13][CH2:14][C@@H:15]2[C@H:16]([CH3:19])[CH2:17][OH:18].CCOCC>O>[NH2:1][C:7]1[C:27](=[O:28])[CH2:26][CH2:25][C@@:24]2([CH3:29])[C:8]=1[CH2:9][CH2:10][C@@H:11]1[C@@H:23]2[CH2:22][CH2:21][C@@:20]2([CH3:30])[C@H:12]1[CH2:13][CH2:14][C@@H:15]2[C@H:16]([CH3:19])[CH2:17][OH:18]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 3283Diethyl EtherHCID 86745915HCID 86745915, compound

Product 1

HCID 10427683HCID 10427683, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-78 °C

Procedure

Ammonia (about 8 mL) was condensed into a Carius tube which contained (20S)-4-chloro-21-hydroxy-20-methylpregn-4-en-3-one acetate (1.5 g, 3.69 mmol) and which was cooled to -78° C. The tube was sealed, heated to 70° C. for one hour, and then allowed to stand at room temperature overnight. The contents of the tube were poured into a mixture of ether and water and the two layers were separated. The organic layer was extracted with 0.5N hydrochloric acid and the resulting acidic, aqueous solution was washed with ether and then made alkaline with 1N aqueous sodium hydroxide. The resulting alkaline, aqueous mixture was extracted with ether and the ether extracts were dried over magnesium sulfate and concentrated to a yellow, foamy solid. This residue was dissolved in methanol (25 mL) and 2N hydrochloric acid (2 mL) and the resulting mixture was heated to reflux for 15 minutes and then allowed to cool to room temperature. The mixture was extracted with ether, then made alkaline with solid sodium carbonate, and extracted with ether. The organic extracts of the alkaline, aqueous solution were dried over magnesium sulfate and concentrated to give (20S)-4-amino-21-hydroxy-20-methylpregn-4-en-3-one as an off-white solid (50 mg, 4%). This compound has the following structure: ##STR7##

Workup

  1. customcondensed into a Carius tube which
  2. customThe tube was sealed
  3. temperatureheated to 70° C. for one hour
  4. customthe two layers were separated
  5. extractionThe organic layer was extracted with 0.5N hydrochloric acid
  6. washthe resulting acidic, aqueous solution was washed with ether
  7. extractionThe resulting alkaline, aqueous mixture was extracted with ether
  8. dry with materialthe ether extracts were dried over magnesium sulfate
  9. concentrationconcentrated to a yellow, foamy solid
  10. dissolutionThis residue was dissolved in methanol (25 mL)
  11. temperature2N hydrochloric acid (2 mL) and the resulting mixture was heated
  12. temperatureto reflux for 15 minutes
  13. temperatureto cool to room temperature
  14. extractionThe mixture was extracted with ether
  15. extractionextracted with ether
  16. dry with materialThe organic extracts of the alkaline, aqueous solution were dried over magnesium sulfate
  17. concentrationconcentrated

Sources & evidence

ORD record
ord-0b9f77d0712c4d2b954cbc5baeff35b3
Source dataset
uspto-grants-1992_06
Patent number
US05120840

Reaction notes

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