p-nitrobenzyl (1R,3R,5R,6S)-6-[(R)-1-hydroxyethyl]-2-oxo-1-methylcarbapenam-3-carboxylate → HCID 91538965, compound

HRID 1840470Notes

Reaction equation

HRID 1840470 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[CH:32]=[CH:31][C:30]([S:33]([C:36]2[N:37]=[CH:38][N:39]3[CH:43]=[C:42]([Sn](CCCC)(CCCC)CCCC)[S:41][C:40]=23)(=[O:35])=[O:34])=[CH:29][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:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][CH:21]=3)=[O:13])=[C:8]([C:42]3[S:41][C:40]4=[C:36]([S:33]([C:30]5[CH:31]=[CH:32][N:27]=[CH:28][CH:29]=5)(=[O:35])=[O:34])[N:37]=[CH:38][N:39]4[CH:43]=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 23447676HCID 23447676, compound

Product 1

HCID 91538965HCID 91538965, compoundYield 55.1%

Procedure

The procedure of Example 1a) was repeated, except that 503 mg of 4-nitrobenzyl (1R,3R,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-oxo-1-carbapenam-3-carboxylate and 808 mg of 7-(pyridin-4-yl)sulfonyl-2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole were used as the starting compounds. Thus, 466 mg of 4-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-[7-(pyridin-4-yl)sulfonylimidazo[5,1-b]thiazol-2-yl]-1-carbapen-2-em-3-carboxylate was prepared.

Sources & evidence

ORD record
ord-f6c6ed28ff50435d8135eb7582dfde5a
Source dataset
uspto-grants-2004_01
Patent number
US06680313B2

Reaction notes

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