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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1037632Generated: October 31, 2026

(+-)-Methionine → Oxymorphone

https://huagongshe.com/reaction/1037632

Reaction equation

Participants

RoleNameHCIDCharge
Reactant(+-)-MethionineHCID 876—
ReactantMethanesulfonic AcidHCID 6395—
ReactantOxycodoneHCID 5284603—
SolventCyclohexaneHCID 8078—
ProductOxymorphoneHCID 5284604—

Reaction Conditions

Temperature17.5 °C

Reaction Steps

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

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08546572B2
Source datasetuspto-grants-2013_10
ORD IDord-7a59f33a2d6740b1b3b227357dfd6211
Source noteuspto-grants-2013_10