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

HRID 2059202노트

반응식

C[O:2][C:3]1C=CC2C[C@H]3NCC[C@]45[C@H](C(CC[C@@]34O)=O)O[C:4]=1C=25.[CH3:23][N:24]1[C@@H:41]2[CH2:42][C:29]3[CH:30]=[CH:31][C:32]([O:44][CH3:45])=[C:33]4[O:34][C@H:35]5[C:36]([CH2:38][CH2:39][C@:40]2([OH:43])[C@:27]5([C:28]=34)[CH2:26][CH2:25]1)=[O:37].C(OC(=O)C)(=O)C>>[CH3:4][C:3]([O:43][C@@:40]12[C@H:41]3[CH2:42][C:29]4[CH:30]=[CH:31][C:32]([O:44][CH3:45])=[C:33]5[O:34][C@H:35]([C@@:27]1([C:28]=45)[CH2:26][CH2:25][N:24]3[CH3:23])[C:36](=[O:37])[CH2:38][CH2:39]2)=[O:2]

참가 물질

반응물 3

HCID 7918Acetic Anhydride

HCID 5284603Oxycodone2회

HCID 5489120Noroxycodone

생성물 1

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

실험 절차

The noroxycodone used as starting material for Method II is prepared from oxycodone by the following steps: ##STR13## Oxycodone is refluxed with acetic anhydride to yield 14-acetyloxycodone. This product is reacted with cyanogen bromide to yield 14-acetyloxy-17-cyano-7,8-dihydronorcodone which is in turn converted to noroxycodone by reaction with hydrogen chloride. The oxycodone starting material is prepared according to M. Freund and E. Speyer, J. fur Praktische Chemie, 94, 135-137 (1916), the disclosure of which is hereby incorporated by reference.

출처 및 근거

ORD 기록: ord-08bc049ccee843f08ff129046415ccb1
출처 데이터셋: uspto-grants-1982_03
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US04322426

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