p-nitrobenzyl (1R,3R,5R,6S)-6-[(R)-1-hydroxyethyl]-2-oxo-1-methylcarbapenam-3-carboxylate → HCID 90822526, 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:68]=[CH:67][C:33]([CH2:34][O:35][C:36]([NH:38][S:39]([NH:42][CH2:43][CH2:44][S:45][C:46]2[N:47]=[CH:48][N:49]3[CH:53]=[C:52]([Sn](CCCC)(CCCC)CCCC)[S:51][C:50]=23)(=[O:41])=[O:40])=[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:52]3[S:51][C:50]4=[C:46]([S:45][CH2:44][CH2:43][NH:42][S:39]([NH:38][C:36]([O:35][CH2:34][C:33]5[CH:67]=[CH:68][C:30]([N+:27]([O-:29])=[O:28])=[CH:31][CH:32]=5)=[O:37])(=[O:40])=[O:41])[N:47]=[CH:48][N:49]4[CH:53]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3]Participants
3
Procedure
The procedure of Example 1a) was repeated, except that 54 mg of 4-nitrobenzyl (1R,3R,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-oxo-1-carbapenam-3-carboxylate and 116 mg of 7-[2-(4-nitrobenzyloxycarbonyl)aminosulfonylaminoethyl]thio-2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole were used as the starting compounds. Thus, 31.8 mg of 4-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-[7-[2-(4-nitrobenzyloxycarbonyl)aminosulfonylaminoethyl]thioimidazo[5,1-b]thiazol-2-yl]-1-carbapen-2-em-3-carboxylate was prepared.
Sources & evidence
- ORD record
- ord-13325475fe37492f80a2137516213b73
- Source dataset
- uspto-grants-2004_01
- Patent number
- US06680313B2
Reaction notes
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