p-nitrobenzyl (1R,3R,5R,6S)-6-[(R)-1-hydroxyethyl]-2-oxo-1-methylcarbapenam-3-carboxylate → 4-Nitrobenzyl (1s,5r,6s)-6-((1r)-1-hydroxyethyl)-1-methyl-2-[7-[(2s)-1-(4-nitrobenzyloxycarbonyl)-pyrrolidin-2-yl]carbonylimidazo[5,1-b]thiazol-2-yl]-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]([C:30]1[CH:67]=[CH:66][C:33]([CH2:34][O:35][C:36]([N:38]2[CH2:42][CH2:41][CH2:40][C@H:39]2[C:43]([C:45]2[N:46]=[CH:47][N:48]3[CH:52]=[C:51]([Sn](CCCC)(CCCC)CCCC)[S:50][C:49]=23)=[O:44])=[O:37])=[CH:32][CH:31]=1)([O-:29])=[O:28]>>[OH:1][C@@H:2]([C@H:4]1[C:25](=[O:26])[N:6]2[C: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]([C:51]3[S:50][C:49]4=[C:45]([C:43]([C@@H:39]5[CH2:40][CH2:41][CH2:42][N:38]5[C:36]([O:35][CH2:34][C:33]5[CH:66]=[CH:67][C:30]([N+:27]([O-:29])=[O:28])=[CH:31][CH:32]=5)=[O:37])=[O:44])[N:46]=[CH:47][N:48]4[CH:52]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3]Participants
3
Reactant 2
Product 1
Procedure
4-Nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-[7-[(2S)-1-(4-nitrobenzyloxycarbonyl)-pyrrolidin-2-yl]carbonylimidazo[5,1-b]thiazol-2-yl]-1-carbapen-2-em-3-carboxylate (1.40 g) was prepared in the same manner as in step a) of Example 1, except that 926 mg of 4-nitrobenzyl (1R,3R,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-oxo-1-carbapenam-3-carboxylate and 1.85 g of 7-[(2S)-1-(4-nitrobenzyloxycarbonyl)-pyrrolidin-2-yl]carbonyl-2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole were used as the starting compounds.
Sources & evidence
- ORD record
- ord-78e242462ac94a1eb2d67918d74cdea4
- Source dataset
- uspto-grants-2005_06
- Patent number
- US06908913B2
Reaction notes
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