(+-)-Methionine → Oxymorphone

HRID 1037632Notes

Reaction equation

HRID 1037632 reaction equation
NC(C(O)=O)CCSC.CS(O)(=O)=O.[O:15]1[C@@H:27]2[C@@:28]34[CH2:30][CH2:31][N:32]([CH3:33])[C@@H:22]([C@:23]3([OH:35])[CH2:24][CH2:25][C:26]2=[O:34])[CH2:21][C:20]2=[C:29]4[C:16]1=[C:17]([O:36]C)[CH:18]=[CH:19]2>C1CCCCC1>[O:15]1[C@@H:27]2[C@@:28]34[CH2:30][CH2:31][N:32]([CH3:33])[C@@H:22]([C@:23]3([OH:35])[CH2:24][CH2:25][C:26]2=[O:34])[CH2:21][C:20]2=[C:29]4[C:16]1=[C:17]([OH:36])[CH:18]=[CH:19]2

Participants

5

Reactant 3

HCID 876(+-)-MethionineHCID 6395Methanesulfonic AcidHCID 5284603Oxycodone

Product 1

HCID 5284604Oxymorphone

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Conditions

Temperature
17.5 °C

Procedure

30 kg of DL-Methionine was added to a solution of methane sulphonic acid (390 kg) maintained at 15-20° C. and stirred for 30 minutes. To this solution, 4,5α-Epoxy-14-hydroxy-3-methoxy-17-methylmorphinan-6-one (40 kg) was added at 20° C. and the reaction mass was heated to 50-55° C. the reaction mixture was maintained at 50-55° C. for 12.0 hrs. After reaction completion, it was quenched in a mixture of methanol (400 L) and water (800 L) and the pH of the resultant solution was adjusted to 9-9.2 with aqueous ammonia at below 20° C. The product was extracted with methylene dichloride and concentrated to obtain the product which was isolated with cyclohexane. Yield: 33.4 kg

Workup

  1. temperaturethe reaction mass was heated to 50-55° C. the reaction mixture
  2. temperaturewas maintained at 50-55° C. for 12.0 hrs
  3. customAfter reaction completion, it
  4. customwas quenched in a mixture of methanol (400 L) and water (800 L)
  5. customwas adjusted to 9-9.2 with aqueous ammonia at below 20° C
  6. extractionThe product was extracted with methylene dichloride
  7. concentrationconcentrated
  8. customto obtain the product which

Sources & evidence

ORD record
ord-7a59f33a2d6740b1b3b227357dfd6211
Source dataset
uspto-grants-2013_10
Patent number
US08546572B2

Reaction notes

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