p-nitrobenzyl (1R,3R,5R,6S)-6-[(R)-1-hydroxyethyl]-2-oxo-1-methylcarbapenam-3-carboxylate → HCID 91285261, compound

HRID 1072367Notes

Reaction equation

HRID 1072367 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]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[C:29]([C:37]([C:39]2[N:40]=[CH:41][N:42]3[CH:46]=[C:45]([Sn](CCCC)(CCCC)CCCC)[S:44][C:43]=23)=[O:38])[CH:28]=1>>[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:45]3[S:44][C:43]4=[C:39]([C:37]([C:29]5[CH:28]=[N:27][C:36]6[C:31]([CH:30]=5)=[CH:32][CH:33]=[CH:34][CH:35]=6)=[O:38])[N:40]=[CH:41][N:42]4[CH:46]=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 22390227HCID 22390227, compound

Product 1

HCID 91285261HCID 91285261, compoundYield 42.4%

Procedure

4-Nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-[7-(quinolin-3-yl)carbonylimidazo[5,1-b]-thiazol-2-yl]-1-carbapen-2-em-3-carboxylate (86 mg) was prepared in substantially the same manner as in step a) of Example 1, except that 180 mg of 4-nitrobenzyl (1R,3R,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-oxo-1-carbapenam-3-carboxylate and 185 mg of 7-(quinolin-3-yl)carbonyl-2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole were used as the starting compounds.

Sources & evidence

ORD record
ord-a7b607e81a5c4736a7f1f4fed5b92632
Source dataset
uspto-grants-2005_06
Patent number
US06908913B2

Reaction notes

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