p-nitrobenzyl (1R,3R,5R,6S)-6-[(R)-1-hydroxyethyl]-2-oxo-1-methylcarbapenam-3-carboxylate → HCID 91423358, compound

HRID 1072386Notes

Reaction equation

HRID 1072386 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].[Cl:27][C:28]1[N:35]2[C:31]([S:32][C:33]([Sn](CCCC)(CCCC)CCCC)=[CH:34]2)=[C:30]([C:49]([C:51]2[CH:52]=[N:53][CH:54]=[CH:55][CH:56]=2)=[O:50])[N:29]=1>>[Cl:27][C:28]1[N:35]2[C:31]([S:32][C:33]([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:34]2)=[C:30]([C:49]([C:51]2[CH:52]=[N:53][CH:54]=[CH:55][CH:56]=2)=[O:50])[N:29]=1

Participants

3

Reactant 2

HCID 13504349p-nitrobenzyl (1R,3R,5R,6S)-6-[(R)-1-hydroxyethyl]-2-oxo-1-methylcarbapenam-3-carboxylateHCID 22390376HCID 22390376, compound

Product 1

HCID 91423358HCID 91423358, compoundYield 89.5%

Procedure

4-Nitrobenzyl (1S,5R,6S)-2-[5-chloro-7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate (712 mg) was prepared in the same manner as in step a) of Example 1, except that 474 mg of 4-nitrobenzyl (1R,3R,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-oxo-1-carbapenam-3-carboxylate and 730 mg of 5-chloro-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-6ed525895dde41fa8484747fe52422dc
Source dataset
uspto-grants-2005_06
Patent number
US06908913B2

Reaction notes

Loading…