p-nitrobenzyl (1R,3R,5R,6S)-6-[(R)-1-hydroxyethyl]-2-oxo-1-methylcarbapenam-3-carboxylate → HCID 91074096, compound

HRID 1840467Notes

Reaction equation

HRID 1840467 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]([CH2:30][C@@H:31]([O:55][Si:56]([CH2:61][CH3:62])([CH2:59][CH3:60])[CH2:57][CH3:58])[CH2:32][S:33][C:34]1[N:35]=[CH:36][N:37]2[CH:41]=[C:40]([Sn](CCCC)(CCCC)CCCC)[S:39][C:38]=12)=[N+:28]=[N-:29]>>[N:27]([CH2:30][C@@H:31]([O:55][Si:56]([CH2:59][CH3:60])([CH2:61][CH3:62])[CH2:57][CH3:58])[CH2:32][S:33][C:34]1[N:35]=[CH:36][N:37]2[CH:41]=[C:40]([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])[S:39][C:38]=12)=[N+:28]=[N-:29]

Participants

3

Reactant 2

HCID 13504349p-nitrobenzyl (1R,3R,5R,6S)-6-[(R)-1-hydroxyethyl]-2-oxo-1-methylcarbapenam-3-carboxylateHCID 131724320HCID 131724320, compound

Product 1

HCID 91074096HCID 91074096, compoundYield 48.8%

Procedure

The procedure of Example 1a) was repeated, except that 582 mg of 4-nitrobenzyl (1R,3R,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-oxo-1-carbapenam-3-carboxylate and 1.11 g of 7-((2R)-3-azido-2-triethylsilyloxypropyl)thio-2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole were used as the starting compounds. Thus, 560 mg of 4-nitrobenzyl (1S,5R,6S)-2-[7-((2R)-3-azido-2-triethylsilyloxypropyl)thioimidazo[5,1-b]thiazol-2-yl]-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate was prepared.

Sources & evidence

ORD record
ord-4424f30a25404e44bd7f5f18a866403c
Source dataset
uspto-grants-2004_01
Patent number
US06680313B2

Reaction notes

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