p-nitrobenzyl (1R,3R,5R,6S)-6-[(R)-1-hydroxyethyl]-2-oxo-1-methylcarbapenam-3-carboxylate → HCID 91269457, 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].[C:27]1([C:33]2[CH:34]=[C:35]([C:39]([C:41]3[N:42]=[CH:43][N:44]4[CH:48]=[C:47]([Sn](CCCC)(CCCC)CCCC)[S:46][C:45]=34)=[O:40])[CH:36]=[N:37][CH:38]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[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:47]3[S:46][C:45]4=[C:41]([C:39]([C:35]5[CH:36]=[N:37][CH:38]=[C:33]([C:27]6[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=6)[CH:34]=5)=[O:40])[N:42]=[CH:43][N:44]4[CH:48]=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-phenylpyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-1-carbapen-2-em-3-carboxylate (47 mg) was prepared in substantially the same manner as in step a) of Example 1, except that 270 mg of 4-nitrobenzyl (1R,3R,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-oxo-1-carbapenam-3-carboxylate and 293 mg of 7-(5-phenylpyridin-3-yl)carbonyl-2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole were used as the starting compounds.
Sources & evidence
- ORD record
- ord-97f44c255e6d47e49189c71855489966
- Source dataset
- uspto-grants-2005_06
- Patent number
- US06908913B2
Reaction notes
Loading…