Hydrochloric Acid → Oxycodone

HRID 1478419

반응식

HRID 1478419 반응식
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]

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 6049Ethylenediaminetetraacetic Acid2회HCID 5086465Acetic acid, mercapto-, ion(1-)HCID 5284603OxycodoneHCID 23690444Sodium Thioglycolate

생성물 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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-42daa6cc3ad1428a8d051dbe3e85dcb3
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09403838B2

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