Hydrochloric Acid → HCID 22842379, compound

HRID 1836168Notes

Reaction equation

HRID 1836168 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) added in 2 ml ethanol. This was refluxed for 2 hr, then the flask was cooled in an ice-water bath. The pH was adjusted to 3 with 12 N 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 the desired product was recovered.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux
  3. temperatureThis was refluxed for 2 hr
  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 the desired product was recovered

Sources & evidence

ORD record
ord-e06f85bf135b4e77a80cb647d780dc9b
Source dataset
uspto-grants-2004_08
Patent number
US06777190B1

Reaction notes

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