Hydrochloric Acid → Oxycodone

HRID 574357

Reaktionsgleichung

Reaktionsgleichung von HRID 574357
Cl.[CH3:2][N:3]1[C@@H:20]2[CH2:21][C:8]3[CH:9]=[CH:10][C:11]([O:23][CH3:24])=[C:12]4[O:13][C@H:14]5[C:15]([CH2:17][CH2:18][C@:19]2([OH:22])[C@:6]5([C:7]=34)[CH2:5][CH2:4]1)=[O:16].C(N(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=O.C([O-])(=O)CS.[Na+].C([O-])(=O)CS>>[CH3:2][N:3]1[C@@H:20]2[CH2:21][C:8]3[CH:9]=[CH:10][C:11]([O:23][CH3:24])=[C:12]4[O:13][C@H:14]5[C:15]([CH2:17][CH2:18][C@:19]2([OH:22])[C@:6]5([C:7]=34)[CH2:5][CH2:4]1)=[O:16].[CH3:2][N:3]1[C@@H:20]2[CH2:21][C:8]3[CH:9]=[CH:10][C:11]([O:23][CH3:24])=[C:12]4[O:13][CH:14]5[C:15]([CH:17]=[CH:18][C@:19]2([OH:22])[C@:6]5([C:7]=34)[CH2:5][CH2:4]1)=[O:16]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 6049Ethylenediaminetetraacetic Acid2×HCID 5086465Acetic acid, mercapto-, ion(1-)HCID 5284603OxycodoneHCID 23690444Sodium Thioglycolate

Produkt 2

HCID 5284603OxycodoneHCID 5359420(4R,4aS,12bS)-4a-hydroxy-9-methoxy-3-methyl-2,4,7a,13-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one

Versuchsvorschrift

An oxycodone sample containing more than 300 ppm of 14-hydroxycodeinone was dissolved in water at pH 6.0 to produce a 7.5% solution (75 mg/mL) using 4 M HCl to effect neutralization and dissolution of the oxycodone to pH 6. Sufficient solid EDTA and solid sodium thioglycolate were added to bring the concentrations of these components in the reaction mixture to 2 mM EDTA and 20 mM thioglycolate. The pH was maintained at pH 6.0, at room temperature for 2.8 hours, after which time the reaction mixture was raised to pH 9 to precipitate the oxycodone from the solution containing the thioglycolate-Michael adduct, and excess thioglycolate. The precipitated oxycodone was washed with pH 9, 0.05 M sodium bicarbonate buffer, and dissolved in ethyl acetate. The ethyl acetate solution of oxycodone was extracted with pH 9.0, 0.05 M sodium bicarbonate buffer, and the ethyl acetate removed under reduced pressure to yield oxycodone containing less than 10 ppm of 14-hydroxycodeinone.

Aufarbeitung

  1. temperatureafter which time the reaction mixture was raised to pH 9
  2. customto precipitate the oxycodone from the solution
  3. additioncontaining the thioglycolate-Michael adduct, and excess thioglycolate
  4. washThe precipitated oxycodone was washed with pH 9, 0.05 M sodium bicarbonate buffer
  5. dissolutiondissolved in ethyl acetate
  6. extractionThe ethyl acetate solution of oxycodone was extracted with pH 9.0, 0.05 M sodium bicarbonate buffer
  7. customthe ethyl acetate removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-51307fa2903d449a895c45bf80e8d3fb
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09034893B2

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