p-nitrobenzyl (3R,5R,6S)-6[(R)-1-hydroxyethyl]-2-oxocarbapenam-3-carboxylate → 4-Nitrobenzyl (5r,6s)-2-[7-(2-t-butyldimethylsilyloxyethyl)thio-imidazo[5,1-b]thiazol-2-yl]-6-((1r)-1-hydroxyethyl)-1-carbapen-2-em-3-carboxylate

HRID 1840441Notes

Reaction equation

HRID 1840441 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:24](=[O:25])[N:6]2[C@@H:7]([C:11]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=3)=[O:12])[C:8](=O)[CH2:9][C@H:5]12)[CH3:3].[Si:26]([O:33][CH2:34][CH2:35][S:36][C:37]1[N:38]=[CH:39][N:40]2[CH:44]=[C:43]([Sn](CCCC)(CCCC)CCCC)[S:42][C:41]=12)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]>>[Si:26]([O:33][CH2:34][CH2:35][S:36][C:37]1[N:38]=[CH:39][N:40]2[CH:44]=[C:43]([C:8]3[CH2:9][C@@H:5]4[C@@H:4]([C@H:2]([OH:1])[CH3:3])[C:24](=[O:25])[N:6]4[C:7]=3[C:11]([O:13][CH2:14][C:15]3[CH:16]=[CH:17][C:18]([N+:21]([O-:23])=[O:22])=[CH:19][CH:20]=3)=[O:12])[S:42][C:41]=12)([C:29]([CH3:32])([CH3:30])[CH3:31])([CH3:28])[CH3:27]

Participants

3

Reactant 2

HCID 10154755p-nitrobenzyl (3R,5R,6S)-6[(R)-1-hydroxyethyl]-2-oxocarbapenam-3-carboxylateHCID 178368917-(2-t-Butyldimethylsilyloxyethyl)thio-2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole

Product 1

HCID 915978904-Nitrobenzyl (5r,6s)-2-[7-(2-t-butyldimethylsilyloxyethyl)thio-imidazo[5,1-b]thiazol-2-yl]-6-((1r)-1-hydroxyethyl)-1-carbapen-2-em-3-carboxylateYield 50.5%

Procedure

The procedure of Example 1a) was repeated, except that 752 mg of 4-nitrobenzyl (3R,5R,6S)-6-((1R)-1-hydroxyethyl)-2-oxo-1-carbapenam-3-carboxylate and 1.433 g of 7-(2-t-butyldimethylsilyloxyethyl)thio-2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole were used as the starting compounds. Thus, 703 mg of 4-nitrobenzyl (5R,6S)-2-[7-(2-t-butyldimethylsilyloxyethyl)thioimidazo[5,1-b]thiazol-2-yl]-6-((1R)-1-hydroxyethyl)-1-carbapen-2-em-3-carboxylate was prepared.

Sources & evidence

ORD record
ord-85c2e4fffb124cca91b5f609c07e92f0
Source dataset
uspto-grants-2004_01
Patent number
US06680313B2

Reaction notes

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