Benzyl Bromide → 4-Nitrobenzyl (1s,5r,6s)-2-[7-(1-benzylpyridinium-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-6-((1r)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate bromide

HRID 1072355Notes

Reaction equation

HRID 1072355 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:40](=[O:41])[N:6]2[C:7]([C:27]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=3)=[O:28])=[C:8]([C:11]3[S:15][C:14]4=[C:16]([C:19]([C:21]5[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=5)=[O:20])[N:17]=[CH:18][N:13]4[CH:12]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].[CH2:42]([Br:49])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>C(#N)C>[Br-:49].[CH2:42]([N+:23]1[CH:24]=[CH:25][CH:26]=[C:21]([C:19]([C:16]2[N:17]=[CH:18][N:13]3[CH:12]=[C:11]([C:8]4[C@H:9]([CH3:10])[C@@H:5]5[C@@H:4]([C@H:2]([OH:1])[CH3:3])[C:40](=[O:41])[N:6]5[C:7]=4[C:27]([O:29][CH2:30][C:31]4[CH:32]=[CH:33][C:34]([N+:37]([O-:39])=[O:38])=[CH:35][CH:36]=4)=[O:28])[S:15][C:14]=23)=[O:20])[CH:22]=1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 68934911(4-nitrobenzyl) (1S,5R,6S)-6-[(1R)-1-hydroxyethyl]-2-[7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-1-methylcarbapen-2-em-3-carboxylate

Product 1

HCID 1317250074-Nitrobenzyl (1s,5r,6s)-2-[7-(1-benzylpyridinium-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-6-((1r)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate bromide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-[7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-1-carbapen-2-em-3-carboxylate (78.1 mg) was suspended in 1.5 ml of acetonitrile to prepare a suspension. Benzyl bromide (0.032 ml) was added to the suspension, and the mixture was stirred at room temperature for 10 hr. The reaction solution was concentrated under the reduced pressure to give 4-nitrobenzyl (1S,5R,6S)-2-[7-(1-benzylpyridinium-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate bromide.

Workup

  1. customto prepare a suspension
  2. concentrationThe reaction solution was concentrated under the reduced pressure

Sources & evidence

ORD record
ord-46d9c540c7ad4f5d8a76b8c9d3d90d63
Source dataset
uspto-grants-2005_06
Patent number
US06908913B2

Reaction notes

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