p-nitrobenzyl (1R,3R,5R,6S)-6-[(R)-1-hydroxyethyl]-2-oxo-1-methylcarbapenam-3-carboxylate → HCID 91401074, compound

HRID 1840451Notes

Reaction equation

HRID 1840451 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]([C:30]1[CH:65]=[CH:64][C:33]([CH2:34][O:35][C:36]([NH:38][CH2:39][CH2:40][CH2:41][S:42][C:43]2[N:44]=[CH:45][N:46]3[CH:50]=[C:49]([Sn](CCCC)(CCCC)CCCC)[S:48][C:47]=23)=[O:37])=[CH:32][CH:31]=1)([O-:29])=[O:28]>>[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:49]3[S:48][C:47]4=[C:43]([S:42][CH2:41][CH2:40][CH2:39][NH:38][C:36]([O:35][CH2:34][C:33]5[CH:64]=[CH:65][C:30]([N+:27]([O-:29])=[O:28])=[CH:31][CH:32]=5)=[O:37])[N:44]=[CH:45][N:46]4[CH:50]=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 22631454HCID 22631454, compound

Product 1

HCID 91401074HCID 91401074, compoundYield 63.6%

Procedure

The procedure of Example 1a) was repeated, except that 628 mg of 4-nitrobenzyl (1R,3R,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-oxo-1-carbapenam-3-carboxylate and 1.24 g of 7-[3-(4-nitrobenzyloxycarbonyl)aminopropyl]thio-2-(tri-n-butylstannyl)imidazo[5,1-b]-thiazole were used as the starting compounds. Thus, 812 mg of 4-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-[7-[3-(4-nitrobenzyloxycarbonyl)aminopropyl]thioimidazo[5,1-b]thiazol-2-yl]-1-carbapen-2-em-3-carboxylate were prepared.

Sources & evidence

ORD record
ord-9d019d86712143e79980a2adcc15ff7e
Source dataset
uspto-grants-2004_01
Patent number
US06680313B2

Reaction notes

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