p-nitrobenzyl (1R,3R,5R,6S)-6-[(R)-1-hydroxyethyl]-2-oxo-1-methylcarbapenam-3-carboxylate → 4-Nitrobenzyl (1s,5r,6s)-2-[7-[5-(2-azidoethylthio)pyridin-3-yl]carbonylimidazo[5,1-b]thiazol-2-yl]-6-((1r)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate
Reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:25](=[O:26])[N:6]2[C@@H:7]([C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=3)=[O:13])[C:8](=O)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].[N:27]([CH2:30][CH2:31][S:32][C:33]1[CH:34]=[C:35]([C:39]([C:41]2[N:42]=[CH:43][N:44]3[CH:48]=[C:47]([Sn](CCCC)(CCCC)CCCC)[S:46][C:45]=23)=[O:40])[CH:36]=[N:37][CH:38]=1)=[N+:28]=[N-:29]>>[N:27]([CH2:30][CH2:31][S:32][C:33]1[CH:34]=[C:35]([C:39]([C:41]2[N:42]=[CH:43][N:44]3[CH:48]=[C:47]([C:8]4[C@H:9]([CH3:10])[C@@H:5]5[C@@H:4]([C@H:2]([OH:1])[CH3:3])[C:25](=[O:26])[N:6]5[C:7]=4[C:12]([O:14][CH2:15][C:16]4[CH:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][CH:21]=4)=[O:13])[S:46][C:45]=23)=[O:40])[CH:36]=[N:37][CH:38]=1)=[N+:28]=[N-:29]Participants
3
Reactant 2
Product 1
Procedure
4-Nitrobenzyl (1S,5R,6S)-2-[7-[5-(2-azidoethylthio)pyridin-3-yl]carbonylimidazo[5,1-b]thiazol-2-yl]-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate (370 mg) was prepared in the same manner as in step a) of Example 1, except that 485 mg of 4-nitrobenzyl (1R,3R,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-oxo-1-carbapenam-3-carboxylate and 857 mg of 7-[5-(2-azidoethylthio)pyridin-3-yl]carbonyl-2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole were used as the starting compounds.
Sources & evidence
- ORD record
- ord-2f19d4dacc414cfb823c0ddf2f9039d3
- Source dataset
- uspto-grants-2005_06
- Patent number
- US06908913B2
Reaction notes
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