3',4'-Dehydrovinblastine → methyl (13S,15R,16R,18S)-13-[(1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-10-hydroxy-5-methoxy-10-methoxycarbonyl-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraen-4-yl]-18-ethyl-17-oxa-1,11-diazapentacyclo[13.4.1.04,12.05,10.016,18]icosa-4(12),5,7,9-tetraene-13-carboxylate
Reaction equation
[O-2:1].[Al+3].[O-2].[O-2].[Al+3].[CH3:6][CH2:7][C:8]1[CH2:19][N:17]2[CH2:18][C@H:10]([CH2:11][C@:12]([C:60]([O:62][CH3:63])=[O:61])([C:27]3[CH:32]=[C:31]4[C:33]56[C@@H:44]([N:45]([CH3:46])[C:30]4=[CH:29][C:28]=3[O:58][CH3:59])[C@@:43]([OH:51])([C:47]([O:49][CH3:50])=[O:48])[C@H:42]([O:52][C:53]([CH3:55])=[O:54])[C@:38]3([CH2:56][CH3:57])[CH:39]=[CH:40][CH2:41][N:36]([C@H:37]53)[CH2:35][CH2:34]6)[C:13]3[NH:26][C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:14]=3[CH2:15][CH2:16]2)[CH:9]=1>>[CH3:6][CH2:7][C@@:8]12[O:1][C@@H:9]1[C@H:10]1[CH2:18][N:17]([CH2:16][CH2:15][C:14]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=4[NH:26][C:13]=3[C@@:12]([C:60]([O:62][CH3:63])=[O:61])([C:27]3[CH:32]=[C:31]4[C@:33]56[C@@H:37]7[C@:38]([CH2:56][CH3:57])([C@@H:42]([O:52][C:53]([CH3:55])=[O:54])[C@:43]([OH:51])([C:47]([O:49][CH3:50])=[O:48])[C@@H:44]5[N:45]([CH3:46])[C:30]4=[CH:29][C:28]=3[O:58][CH3:59])[CH:39]=[CH:40][CH2:41][N:36]7[CH2:35][CH2:34]6)[CH2:11]1)[CH2:19]2Participants
3
Reactant 2
Product 1
Procedure
Following the procedure described in the Example 19 but performing the oxidation in the presence of aluminium oxide used in a five-fold amount related to the anhydrovinblastine the title compound is prepared. The quality of the aluminium oxide employed corresponds to the activity grade I or II. The reaction is completed within two hours.
Sources & evidence
- ORD record
- ord-b4512ff0f39047f8a868dcdd7e930e22
- Source dataset
- uspto-grants-1980_04
- Patent number
- US04199505
Linked notes
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