Hydrochloric Acid → Oxycodone

HRID 254267

Reaction equation

HRID 254267 reaction equation
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]

Participants

7

Reactant 5

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

Product 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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a040a0d05a854401972464bb2c39f036
Source dataset
uspto-grants-2011_01
Patent number
US07875623B2

Linked notes

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