p-nitrobenzyl (1R,3R,5R,6S)-6-[(R)-1-hydroxyethyl]-2-oxo-1-methylcarbapenam-3-carboxylate → HCID 91347015, 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].[N+:27]([C:30]1[CH:75]=[CH:74][C:33]([CH2:34][O:35][C:36]([N:38]2[CH2:43][CH2:42][N:41]([CH2:44][C:45]3[CH:46]=[C:47]([C:51]([C:53]4[N:54]=[CH:55][N:56]5[CH:60]=[C:59]([Sn](CCCC)(CCCC)CCCC)[S:58][C:57]=45)=[O:52])[CH:48]=[N:49][CH:50]=3)[CH2:40][CH2:39]2)=[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:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][CH:21]=3)=[O:13])=[C:8]([C:59]3[S:58][C:57]4=[C:53]([C:51]([C:47]5[CH:48]=[N:49][CH:50]=[C:45]([CH2:44][N:41]6[CH2:42][CH2:43][N:38]([C:36]([O:35][CH2:34][C:33]7[CH:74]=[CH:75][C:30]([N+:27]([O-:29])=[O:28])=[CH:31][CH:32]=7)=[O:37])[CH2:39][CH2:40]6)[CH:46]=5)=[O:52])[N:54]=[CH:55][N:56]4[CH:60]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3]Participants
3
Procedure
4-Nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-[7-[5-[4-(4-nitrobenzyloxycarbonyl)piperazin-1-yl]methylpyridin-3-yl]carbonylimidazo[5,1-b]thiazol-2-yl]-1-carbapen-2-em-3-carboxylate (172 mg) was prepared in the same manner as in step a) of Example 1, except that 337 mg of 4-nitrobenzyl (1R,3R,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-oxo-1-carbapenam-3-carboxylate and 780 mg of 7-[5-[4-(4-nitrobenzyloxycarbonyl)-piperazin-1-yl]methylpyridin-3-yl]carbonyl-2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole were used as the starting compounds.
Sources & evidence
- ORD record
- ord-18fd364a126f4a4cb8085c904503f955
- Source dataset
- uspto-grants-2005_06
- Patent number
- US06908913B2
Reaction notes
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