p-nitrobenzyl (1R,3R,5R,6S)-6-[(R)-1-hydroxyethyl]-2-oxo-1-methylcarbapenam-3-carboxylate → HCID 90966134, compound

HRID 1072378Notes

Reaction equation

HRID 1072378 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@@H:30]1[CH2:34][N:33]([C:35]([O:37][CH2:38][C:39]2[CH:44]=[CH:43][C:42]([N+:45]([O-:47])=[O:46])=[CH:41][CH:40]=2)=[O:36])[C@H:32]([C:48]([C:50]2[N:51]=[CH:52][N:53]3[CH:57]=[C:56]([Sn](CCCC)(CCCC)CCCC)[S:55][C:54]=23)=[O:49])[CH2:31]1)=[N+:28]=[N-:29]>>[N:27]([C@@H:30]1[CH2:34][N:33]([C:35]([O:37][CH2:38][C:39]2[CH:44]=[CH:43][C:42]([N+:45]([O-:47])=[O:46])=[CH:41][CH:40]=2)=[O:36])[C@H:32]([C:48]([C:50]2[N:51]=[CH:52][N:53]3[CH:57]=[C:56]([C:8]4[C@H:9]([CH3:10])[C@@H:5]5[C@@H:4]([C@H:2]([OH:1])[CH3:3])[C:25](=[O:26])[N:6]5[C:7]=4[C:12]([O:14][CH2:15][C:16]4[CH:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][CH:21]=4)=[O:13])[S:55][C:54]=23)=[O:49])[CH2:31]1)=[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 86591210HCID 86591210, compound

Product 1

HCID 90966134HCID 90966134, compound

Procedure

A crude compound (261 mg) of 4-nitrobenzyl (1S,5R,6S)-2-[7-[(2S,4S)-4-azido-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-2-yl]carbonylimidazo[5,1-b]thiazol-2-yl]-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate was prepared in the same manner as in Example, except that 157 mg of 4-nitrobenzyl (1R,3R,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-oxo-1-carbapenam-3-carboxylate and 321 mg of 7-[(2S,4S)-4-azido-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-2-yl]carbonyl-2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole were used as the starting compounds.

Sources & evidence

ORD record
ord-4a7070d63c6346ada4f7364885875540
Source dataset
uspto-grants-2005_06
Patent number
US06908913B2

Reaction notes

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