Hydrochloric Acid → HCID 22842379, compound

HRID 1534325Notes

Reaction equation

HRID 1534325 reaction equation
S(O)(O)(=O)=O.[CH:6]1[C:22]2[CH2:21][C@H:20]3[N:23]([CH2:25][CH2:26][C@@:12]45[C@H:19]3[CH:18]=[CH:17][C@H:15]([OH:16])[C@@H:13]4[O:14][C:10]([C:11]=25)=[C:8]([OH:9])[CH:7]=1)[CH3:24].C(=O)([O-])[O-].[K+].[K+].Br[CH2:34][C:35]([OH:37])=[O:36].[ClH:38]>C(O)C>[ClH:38].[C:35]([CH2:34][O:9][C:8]1[CH:7]=[CH:6][C:22]2[CH2:21][C@H:20]3[N:23]([CH3:24])[CH2:25][CH2:26][C@:12]45[C:11]=2[C:10]=1[O:14][C@H:13]4[C@@H:15]([OH:16])[CH:17]=[CH:18][C@@H:19]35)([OH:37])=[O:36]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6227Bromoacetic AcidHCID 11430Potassium CarbonateHCID 546428064-31-3

Product 1

HCID 22842379HCID 22842379, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Morphine sulfate (1.67 g, 5×10-3 mol) was dissolved with potassium carbonate (2.07 g, 1.5×10-2 mol) in 80 ml ethanol. The solution was heated to reflux while stirring and a solution containing bromoacetic acid (0.7 g, 5×10-3 mol) was added in 2 ml ethanol. This was refluxed for two hours, then the flask was cooled in an ice water bath. The pH was adjusted to 3 with 12N hydrochloric acid and precipitates were filtered. Solvents were evaporated under vacuum and 10 ml ethanol was added to the residue. Precipitates were filtered and solvents evaporated under vacuum. The residue was recrystallized from water/acetone (10:90). Approximately 300 mg of product was recovered.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux
  3. temperatureThis was refluxed for two hours
  4. temperaturethe flask was cooled in an ice water bath
  5. customprecipitates
  6. filtrationwere filtered
  7. customSolvents were evaporated under vacuum and 10 ml ethanol
  8. additionwas added to the residue
  9. customPrecipitates
  10. filtrationwere filtered
  11. customsolvents evaporated under vacuum
  12. customThe residue was recrystallized from water/acetone (10:90)
  13. customApproximately 300 mg of product was recovered

Sources & evidence

ORD record
ord-3ad07387f9b74d26a69b6334747f612e
Source dataset
uspto-grants-1992_02
Patent number
US05089391

Reaction notes

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