p-nitrobenzyl (1R,3R,5R,6S)-6-[(R)-1-hydroxyethyl]-2-oxo-1-methylcarbapenam-3-carboxylate → HCID 91366763, compound
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].[Si:27]([O:34][C@H:35]1[CH2:39][N:38]([C:40]([O:42][CH2:43][C:44]2[CH:49]=[CH:48][C:47]([N+:50]([O-:52])=[O:51])=[CH:46][CH:45]=2)=[O:41])[C@H:37]([C:53]([C:55]2[N:56]=[CH:57][N:58]3[CH:62]=[C:61]([Sn](CCCC)(CCCC)CCCC)[S:60][C:59]=23)=[O:54])[CH2:36]1)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28]>>[Si:27]([O:34][C@H:35]1[CH2:39][N:38]([C:40]([O:42][CH2:43][C:44]2[CH:45]=[CH:46][C:47]([N+:50]([O-:52])=[O:51])=[CH:48][CH:49]=2)=[O:41])[C@H:37]([C:53]([C:55]2[N:56]=[CH:57][N:58]3[CH:62]=[C:61]([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:60][C:59]=23)=[O:54])[CH2:36]1)([C:30]([CH3:31])([CH3:32])[CH3:33])([CH3:29])[CH3:28]Participants
3
Procedure
4-Nitrobenzyl (1S,5R,6S)-2-[7-[(2S,4R)-4-t-butyldimethylsilyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-2-yl]carbonylimidazo[5,1-b]thiazol-2-yl]-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate (369 mg) was prepared in the same manner as in step a) of Example 1, except that 312 mg of 4-nitrobenzyl (1R,3R,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-oxo-1-carbapenam-3-carboxylate and 707 mg of 7-[(2S,4R)-4-t-butyldimethylsilyloxy-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-926f659a12034ab198a5a3a03003e962
- Source dataset
- uspto-grants-2005_06
- Patent number
- US06908913B2
Reaction notes
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