Hydroxylamine → (3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl)oxy-14-ethyl-7,12,13-trihydroxy-10-hydroxyimino-4-((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl)oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one
Reaction equation
[CH3:1][CH2:2][C@H:3]1[O:18][C:16](=[O:17])[C@H:15]([CH3:19])[C@@H:14]([O:20][C@@H:21]2[O:26][C@@H:25]([CH3:27])[C@H:24]([OH:28])[C@@:23]([O:30][CH3:31])([CH3:29])[CH2:22]2)[C@H:13]([CH3:32])[C@@H:12]([O:33][C@@H:34]2[O:39][C@H:38]([CH3:40])[CH2:37][C@H:36]([N:41]([CH3:43])[CH3:42])[C@H:35]2[OH:44])[C@@:11]([OH:46])([CH3:45])[CH2:10][C@@H:9]([CH3:47])[C:7](=O)[C@H:6]([CH3:48])[C@@H:5]([OH:49])[C@@:4]1([OH:51])[CH3:50].[NH2:52][OH:53]>>[CH3:1][CH2:2][C@H:3]1[O:18][C:16](=[O:17])[C@H:15]([CH3:19])[C@@H:14]([O:20][C@@H:21]2[O:26][C@@H:25]([CH3:27])[C@H:24]([OH:28])[C@@:23]([O:30][CH3:31])([CH3:29])[CH2:22]2)[C@H:13]([CH3:32])[C@@H:12]([O:33][C@@H:34]2[O:39][C@H:38]([CH3:40])[CH2:37][C@H:36]([N:41]([CH3:43])[CH3:42])[C@H:35]2[OH:44])[C@@:11]([OH:46])([CH3:45])[CH2:10][C@@H:9]([CH3:47])/[C:7](=[N:52]\[OH:53])/[C@H:6]([CH3:48])[C@@H:5]([OH:49])[C@@:4]1([OH:51])[CH3:50]Participants
3
Reactant 2
Product 1
Procedure
reacting the C-9 ketone of erythromycin A with hydroxylamine to form erythromycin oxime;
Sources & evidence
- ORD record
- ord-4366f10ee0144108909b3c76e3241b69
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06455680B1
Reaction notes
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