p-nitrobenzyl (1R,3R,5R,6S)-6-[(R)-1-hydroxyethyl]-2-oxo-1-methylcarbapenam-3-carboxylate → HCID 90693028, compound

HRID 1840454Notes

Reaction equation

HRID 1840454 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:66]=[CH:65][C:33]([CH2:34][O:35][C:36]([N:38]2[CH2:42][CH2:41][C@H:40]([S:43][C:44]3[N:45]=[CH:46][N:47]4[CH:51]=[C:50]([Sn](CCCC)(CCCC)CCCC)[S:49][C:48]=34)[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:50]3[S:49][C:48]4=[C:44]([S:43][C@H:40]5[CH2:41][CH2:42][N:38]([C:36]([O:35][CH2:34][C:33]6[CH:65]=[CH:66][C:30]([N+:27]([O-:29])=[O:28])=[CH:31][CH:32]=6)=[O:37])[CH2:39]5)[N:45]=[CH:46][N:47]4[CH:51]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3]

Participants

3

Reactant 2

HCID 13504349p-nitrobenzyl (1R,3R,5R,6S)-6-[(R)-1-hydroxyethyl]-2-oxo-1-methylcarbapenam-3-carboxylateHCID 69844058HCID 69844058, compound

Product 1

HCID 90693028HCID 90693028, compoundYield 46%

Procedure

The procedure of Example 1a) was repeated, except that 143 mg of 4-nitrobenzyl (1R,3R,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-oxo-1-carbapenam-3-carboxylate and 287 mg of 7-[(3S)-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-3-yl]thio-2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole were used as the starting compounds. Thus, 136 mg of 4-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-[7-[(3S)-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-3-yl]thioimidazo[5,1-b]thiazol-2-yl]-1-carbapen-2-em-3-carboxylate was prepared.

Sources & evidence

ORD record
ord-418de16ba3354667b0dd527368990122
Source dataset
uspto-grants-2004_01
Patent number
US06680313B2

Reaction notes

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