p-nitrobenzyl (1R,3R,5R,6S)-6-[(R)-1-hydroxyethyl]-2-oxo-1-methylcarbapenam-3-carboxylate → HCID 91519718, compound

HRID 1072395Notes

Reaction equation

HRID 1072395 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].[C:27]([C:30]1[N:37]2[C:33]([S:34][C:35]([Sn](CCCC)(CCCC)CCCC)=[CH:36]2)=[C:32]([C:51]([C:53]2[CH:54]=[N:55][CH:56]=[CH:57][CH:58]=2)=[O:52])[N:31]=1)(=[O:29])[NH2:28]>>[C:27]([C:30]1[N:37]2[C:33]([S:34][C:35]([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:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][CH:21]=3)=[O:13])=[CH:36]2)=[C:32]([C:51]([C:53]2[CH:54]=[N:55][CH:56]=[CH:57][CH:58]=2)=[O:52])[N:31]=1)(=[O:29])[NH2:28]

Participants

3

Reactant 2

HCID 13504349p-nitrobenzyl (1R,3R,5R,6S)-6-[(R)-1-hydroxyethyl]-2-oxo-1-methylcarbapenam-3-carboxylateHCID 22390358HCID 22390358, compound

Product 1

HCID 91519718HCID 91519718, compoundYield 66.9%

Procedure

4-Nitrobenzyl (1S,5R,6S)-2-[5-carbamoyl-7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate (239 mg) was prepared in the same manner as in step a) of Example 1, except that 210 mg of 4-nitrobenzyl (1R,3R,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-oxo-1-carbapenam-3-carboxylate and 342 mg of 5-carbamoyl-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-602eb96345084f6a9b8913ef8882bfc4
Source dataset
uspto-grants-2005_06
Patent number
US06908913B2

Reaction notes

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