p-nitrobenzyl (3R,5R,6S)-6[(R)-1-hydroxyethyl]-2-oxocarbapenam-3-carboxylate → 4-Nitrobenzyl (5r,6s)-6-((1r)-1-hydroxyethyl)-2-[7-[2-(4-nitrobenzyl-oxycarbonyl)aminoethyl]thioimidazo[5,1-b]thiazol-2-yl]-1-carbapen-2-em-3-carboxylate
Reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:24](=[O:25])[N:6]2[C@@H:7]([C:11]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=3)=[O:12])[C:8](=O)[CH2:9][C@H:5]12)[CH3:3].[N+:26]([C:29]1[CH:63]=[CH:62][C:32]([CH2:33][O:34][C:35]([NH:37][CH2:38][CH2:39][S:40][C:41]2[N:42]=[CH:43][N:44]3[CH:48]=[C:47]([Sn](CCCC)(CCCC)CCCC)[S:46][C:45]=23)=[O:36])=[CH:31][CH:30]=1)([O-:28])=[O:27]>>[OH:1][C@@H:2]([C@H:4]1[C:24](=[O:25])[N:6]2[C:7]([C:11]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=3)=[O:12])=[C:8]([C:47]3[S:46][C:45]4=[C:41]([S:40][CH2:39][CH2:38][NH:37][C:35]([O:34][CH2:33][C:32]5[CH:62]=[CH:63][C:29]([N+:26]([O-:28])=[O:27])=[CH:30][CH:31]=5)=[O:36])[N:42]=[CH:43][N:44]4[CH:48]=3)[CH2:9][C@H:5]12)[CH3:3]Participants
3
Reactant 2
Product 1
Procedure
The procedure of Example 1a) was repeated, except that 201 mg of 4-nitrobenzyl (3R,5R,6S)-6-((1R)-1-hydroxyethyl)-2-oxo-1-carbapenam-3-carboxylate and 424 mg of 7-[2-(4-nitrobenzyloxycarbonyl)aminoethyl]thio-2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole were used as the starting compounds. Thus, 200 mg of 4-nitrobenzyl (5R,6S)-6-((1R)-1-hydroxyethyl)-2-[7-[2-(4-nitrobenzyloxycarbonyl)aminoethyl]thioimidazo[5,1-b]thiazol-2-yl]-1-carbapen-2-em-3-carboxylate was prepared.
Sources & evidence
- ORD record
- ord-eacf016e6ae34f868cc169e718478a94
- Source dataset
- uspto-grants-2004_01
- Patent number
- US06680313B2
Reaction notes
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