p-nitrobenzyl (1R,3R,5R,6S)-6-[(R)-1-hydroxyethyl]-2-oxo-1-methylcarbapenam-3-carboxylate → HCID 91493420, compound

HRID 1072397Notes

Reaction equation

HRID 1072397 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]([CH2:30][CH2:31][S:32][C:33]1[N:40]2[C:36]([S:37][C:38]([Sn](CCCC)(CCCC)CCCC)=[CH:39]2)=[C:35]([C:54]([C:56]2[CH:57]=[N:58][CH:59]=[CH:60][CH:61]=2)=[O:55])[N:34]=1)=[N+:28]=[N-:29]>>[N:27]([CH2:30][CH2:31][S:32][C:33]1[N:40]2[C:36]([S:37][C:38]([C:8]3[C@H:9]([CH3:10])[C@@H:5]4[C@@H:4]([C@H:2]([OH:1])[CH3:3])[C:25](=[O:26])[N:6]4[C:7]=3[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])=[CH:39]2)=[C:35]([C:54]([C:56]2[CH:57]=[N:58][CH:59]=[CH:60][CH:61]=2)=[O:55])[N:34]=1)=[N+:28]=[N-:29]

Participants

3

Reactant 2

HCID 13504349p-nitrobenzyl (1R,3R,5R,6S)-6-[(R)-1-hydroxyethyl]-2-oxo-1-methylcarbapenam-3-carboxylateHCID 22390391HCID 22390391, compound

Product 1

HCID 91493420HCID 91493420, compoundYield 50.3%

Procedure

4-Nitrobenzyl (1S,5R,6S)-2-[5-(2-azidoethyl)thio-7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate (853 mg) was prepared in the same manner as in step a) of Example 1, except that 910 mg of 4-nitrobenzyl (1R,3R,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-oxo-1-carbapenam-3-carboxylate and 1.59 g of 5-(2-azidoethyl)thio-7-(pyridin-3-yl)carbonyl-2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole were used as the starting compounds.

Sources & evidence

ORD record
ord-f8c54fdd19f94035b27bdd01d85a7155
Source dataset
uspto-grants-2005_06
Patent number
US06908913B2

Reaction notes

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