Iodoacetamide → 4-Nitrobenzyl (1s,5r,6s)-2-[7-(1-carbamoylmethylpyridinium-3-yl)carbonylimidazo-[5,1-b]thiazol-2-yl]-6-((1r)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate iodide

HRID 1072354Notes

Reaction equation

HRID 1072354 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].[I:42][CH2:43][C:44]([NH2:46])=[O:45]>C(#N)C>[I-:42].[C:44]([CH2:43][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)(=[O:45])[NH2:46]

Participants

4

Reactant 2

HCID 3727IodoacetamideHCID 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 1317250064-Nitrobenzyl (1s,5r,6s)-2-[7-(1-carbamoylmethylpyridinium-3-yl)carbonylimidazo-[5,1-b]thiazol-2-yl]-6-((1r)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate iodideYield 112.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

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 (105.5 mg) was suspended in 2 ml of acetonitrile to prepare a suspension. 2-Iodoacetamide (340 mg) was added to the suspension, and the mixture was stirred at 50° C. for 6 hr. The reaction solution was concentrated under the reduced pressure, 5 ml of ethyl acetate was added to the concentrate, and the insolubles were collected by filtration to give 157 mg of 4-nitrobenzyl (1S,5R,6S)-2-[7-(1-carbamoylmethylpyridinium-3-yl)carbonylimidazo-[5,1-b]thiazol-2-yl]-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate iodide.

Workup

  1. customto prepare a suspension
  2. concentrationThe reaction solution was concentrated under the reduced pressure, 5 ml of ethyl acetate
  3. additionwas added to the concentrate
  4. filtrationthe insolubles were collected by filtration

Sources & evidence

ORD record
ord-19f4772a05064a118720fcfbe9b903c4
Source dataset
uspto-grants-2005_06
Patent number
US06908913B2

Reaction notes

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