Iodoacetamide → 4-Nitrobenzyl (1s,5r,6s)-2-[7-[5-(2-azidoethylthio)-1-carbamoylmethylpyridinium-3-yl]carbonylimidazo[5,1-b]thiazol-2-yl]-6-((1r)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate iodide
Reaction equation
[N:1]([CH2:4][CH2:5][S:6][C:7]1[CH:8]=[C:9]([C:13]([C:15]2[N:16]=[CH:17][N:18]3[CH:22]=[C:21]([C:23]4[C@H:24]([CH3:47])[C@@H:25]5[C@@H:42]([C@H:43]([OH:45])[CH3:44])[C:41](=[O:46])[N:26]5[C:27]=4[C:28]([O:30][CH2:31][C:32]4[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=4)=[O:29])[S:20][C:19]=23)=[O:14])[CH:10]=[N:11][CH:12]=1)=[N+:2]=[N-:3].[I:48][CH2:49][C:50]([NH2:52])=[O:51]>>[I-:48].[N:1]([CH2:4][CH2:5][S:6][C:7]1[CH:8]=[C:9]([C:13]([C:15]2[N:16]=[CH:17][N:18]3[CH:22]=[C:21]([C:23]4[C@H:24]([CH3:47])[C@@H:25]5[C@@H:42]([C@H:43]([OH:45])[CH3:44])[C:41](=[O:46])[N:26]5[C:27]=4[C:28]([O:30][CH2:31][C:32]4[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=4)=[O:29])[S:20][C:19]=23)=[O:14])[CH:10]=[N+:11]([CH2:49][C:50](=[O:51])[NH2:52])[CH:12]=1)=[N+:2]=[N-:3]Participants
3
Reactant 2
Product 1
Procedure
4-Nitrobenzyl (1S,5R,6S)-2-[7-[5-(2-azidoethylthio)-1-carbamoylmethylpyridinium-3-yl]carbonylimidazo[5,1-b]thiazol-2-yl]-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate iodide (140 mg) was prepared in the same manner as in step a) of Example 2, except that 114 mg of 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 and 312 mg of 2-iodoacetamide were used as the starting compounds.
Sources & evidence
- ORD record
- ord-d7bd297af28742c2ad570fabc42ac106
- Source dataset
- uspto-grants-2005_06
- Patent number
- US06908913B2
Reaction notes
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