Acetic Anhydride → (5alpha,14alpha)-3-Methoxy-17-methyl-6-oxo-4,5-epoxymorphinan-14-yl acetate

HRID 2059203Notes

Reaction equation

HRID 2059203 reaction equation
[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:24](OC(=O)C)(=[O:26])[CH3:25]>>[CH3:25][C:24]([O:21][C@@:18]12[C@H:19]3[CH2:20][C:7]4[CH:8]=[CH:9][C:10]([O:22][CH3:23])=[C:11]5[O:12][C@H:13]([C@@:5]1([C:6]=45)[CH2:4][CH2:3][N:2]3[CH3:1])[C:14](=[O:15])[CH2:16][CH2:17]2)=[O:26]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 5284603Oxycodone

Product 1

HCID 13034605(5alpha,14alpha)-3-Methoxy-17-methyl-6-oxo-4,5-epoxymorphinan-14-yl acetate

Procedure

315 g of oxycodone was refluxed with 1600 ml of acetic anhydride for one hour. After cooling the mixture to 50°, acetic anhydride and acetic acid were removed with the rotary evaporator. The solid remaining was dissolved in water and the solution was basified to pH9 with ammonia. The precipitated product was filtered off, washed with water and vacuum dried to yield 357 g of 14-acetyloxycodone (m.p. 215°-216°).

Workup

  1. temperatureAfter cooling the mixture to 50°
  2. customacetic anhydride and acetic acid were removed with the rotary evaporator
  3. dissolutionThe solid remaining was dissolved in water
  4. filtrationThe precipitated product was filtered off
  5. washwashed with water and vacuum
  6. customdried

Sources & evidence

ORD record
ord-0947524abe5c45f28e0903db96a6cc6a
Source dataset
uspto-grants-1982_03
Patent number
US04322426

Reaction notes

Loading…