p-nitrobenzyl (1R,3R,5R,6S)-6-[(R)-1-hydroxyethyl]-2-oxo-1-methylcarbapenam-3-carboxylate → 4-Nitrobenzyl (1s,5r,6s)-6-((1r)-1-hydroxyethyl)-1-methyl-2-[7-(thiophen-2-yl)carbonylimidazo[5,1-b]-thiazol-2-yl]-1-carbapen-2-em-3-carboxylate

HRID 1072362Notes

Reaction equation

HRID 1072362 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].[S:27]1[CH:31]=[CH:30][CH:29]=[C:28]1[C:32]([C:34]1[N:35]=[CH:36][N:37]2[CH:41]=[C:40]([Sn](CCCC)(CCCC)CCCC)[S:39][C:38]=12)=[O:33]>>[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:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=3)=[O:13])=[C:8]([C:40]3[S:39][C:38]4=[C:34]([C:32]([C:28]5[S:27][CH:31]=[CH:30][CH:29]=5)=[O:33])[N:35]=[CH:36][N:37]4[CH:41]=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 223901747-(Thiophen-2-yl)carbonyl-2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole

Product 1

HCID 699578304-Nitrobenzyl (1s,5r,6s)-6-((1r)-1-hydroxyethyl)-1-methyl-2-[7-(thiophen-2-yl)carbonylimidazo[5,1-b]-thiazol-2-yl]-1-carbapen-2-em-3-carboxylateYield 79.9%

Procedure

4-Nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-[7-(thiophen-2-yl)carbonylimidazo[5,1-b]-thiazol-2-yl]-1-carbapen-2-em-3-carboxylate (815 mg) was prepared in the same manner as in step a) of Example 1, except that 640 mg of 4-nitrobenzyl (1R,3R,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-oxo-1-carbapenam-3-carboxylate and 923 mg of 7-(thiophen-2-yl)carbonyl-2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole were used as the starting compounds.

Sources & evidence

ORD record
ord-174fde4ac45445edb1e5eb3c1e4b4165
Source dataset
uspto-grants-2005_06
Patent number
US06908913B2

Reaction notes

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