p-nitrobenzyl (1R,3R,5R,6S)-6-[(R)-1-hydroxyethyl]-2-oxo-1-methylcarbapenam-3-carboxylate → HCID 178462278, 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:81]=[CH:80][C:33]([CH2:34][O:35][C:36]([NH:38][C:39](=[N:66][C:67]([O:69][CH2:70][C:71]2[CH:76]=[CH:75][C:74]([N+:77]([O-:79])=[O:78])=[CH:73][CH:72]=2)=[O:68])[NH:40][CH2:41][CH2:42][CH2:43][S:44][C:45]2[N:46]=[CH:47][N:48]3[CH:52]=[C:51]([Sn](CCCC)(CCCC)CCCC)[S:50][C:49]=23)=[O:37])=[CH:32][CH:31]=1)([O-:29])=[O:28]>>[N+:77]([C:74]1[CH:75]=[CH:76][C:71]([CH2:70][O:69][C:67]([NH:66][C:39](=[N:38][C:36]([O:35][CH2:34][C:33]2[CH:32]=[CH:31][C:30]([N+:27]([O-:29])=[O:28])=[CH:81][CH:80]=2)=[O:37])[NH:40][CH2:41][CH2:42][CH2:43][S:44][C:45]2[N:46]=[CH:47][N:48]3[CH:52]=[C:51]([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:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=4)=[O:13])[S:50][C:49]=23)=[O:68])=[CH:72][CH:73]=1)([O-:79])=[O:78]Participants
3
Procedure
The procedure of Example 1a) was repeated, except that 297 mg of 4-nitrobenzyl (1R,3R,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-oxo-1-carbapenam-3-carboxylate and 777 mg of 7-[3-N,N′-bis(4-nitrobenzyloxycarbonyl)guanidinopropyl]thio-2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole were used as the starting compounds. Thus, 436 mg of 4-nitrobenzyl (1S,5R,6S)-2-[7-[3-N,N′-bis(4-nitrobenzyloxycarbonyl)guanidinopropyl]thioimidazo[5,1-b]thiazol-2-yl]-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate was prepared.
Sources & evidence
- ORD record
- ord-43a88dd9f62d43fc899217462c4caccc
- Source dataset
- uspto-grants-2004_01
- Patent number
- US06680313B2
Reaction notes
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