Ammonium Hydroxide → Oxycodone

HRID 1529460

반응식

HRID 1529460 반응식
[CH3:1][N:2]1[C@@H:19]2[CH2:20][C:7]3[CH:8]=[CH:9][C:10]([O:22][CH3:23])=[C:11]4[O:12][C@H:13]5[C:14]([CH2:16][CH2:17][C@:18]2([OH:21])[C@:5]5([C:6]=34)[CH2:4][CH2:3]1)=[O:15].C([O-])(=O)C.[OH-].[NH4+].S([O-])([O-])(=O)=O.[Na+].[Na+]>C(O)(C)C.C(Cl)(Cl)Cl>[CH3:1][N:2]1[C@@H:19]2[CH2:20][C:7]3[CH:8]=[CH:9][C:10]([O:22][CH3:23])=[C:11]4[O:12][C@H:13]5[C:14]([CH2:16][CH2:17][C@:18]2([OH:21])[C@:5]5([C:6]=34)[CH2:4][CH2:3]1)=[O:15]

참가 물질

6

반응물 3

HCID 14923Ammonium HydroxideHCID 24436Sodium SulfateHCID 86762802(4R,4aS,7aR,12bS)-4a-hydroxy-9-methoxy-3-methyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one acetate

생성물 1

HCID 5284603Oxycodone수율 74.1%

시약·촉매·용매 2

HCID 3776Isopropanol용매HCID 6212Chloroform용매

실험 절차

Oxycodone acetate solution was diluted with isopropanol (25 mL), cooled to 10° C. and neutralized at 10° C. to 5° C. with ammonium hydroxide (conc., ˜30 mL until pH ˜9.5). Stirring continued for 10 minutes and precipitated solids were filtered off, washed on filter with water (20 mL, 2×50 mL, 10 mL) and dried on filter for 0.5 hours. The light gray wet material (22.29 g) was prepared. This material was dissolved in chloroform (150 mL), treated with sodium sulfate (anhydrous) for one hour. Solvent was removed in vacuum and gray powder was dried on rotary evaporator for one hour at 50° C. in the bath, providing oxycodone base (16.31 g, 51.72 mmol, 74.1% yield on ABUK sulfate). Impurity profile is shown in Table 8.

후처리

  1. customprecipitated solids
  2. filtrationwere filtered off
  3. washwashed
  4. filtrationon filter with water (20 mL, 2×50 mL, 10 mL)
  5. customdried
  6. filtrationon filter for 0.5 hours
  7. customSolvent was removed in vacuum and gray powder
  8. customwas dried on rotary evaporator for one hour at 50° C. in the bath

출처 및 근거

ORD 기록
ord-8967d3af79db460493daa70872dc959d
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09090620B2

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