Iodoacetamide → HCID 178462277, compound

HRID 382643Notes

Reaction equation

HRID 382643 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:31](=[O:32])[N:6]2[C:7]([C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=3)=[O:19])=[C:8]([C:10]3[S:14][C:13]4=[CH:15][N:16]=[CH:17][N:12]4[CH:11]=3)[CH2:9][C@H:5]12)[CH3:3].[I:33][CH2:34][C:35]([NH2:37])=[O:36]>CC(C)=O>[I-:33].[C:35]([CH2:34][N:16]1[CH:15]=[C:13]2[S:14][C:10]([C:8]3[CH2:9][C@@H:5]4[C@@H:4]([C@H:2]([OH:1])[CH3:3])[C:31](=[O:32])[N:6]4[C:7]=3[C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=3)=[O:19])=[CH:11][N+:12]2=[CH:17]1)(=[O:36])[NH2:37]

Participants

4

Reactant 2

HCID 3727IodoacetamideHCID 120700434-nitrobenzyl (5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-2-yl)-1-carbapen-2-em-3-carboxylate

Product 1

HCID 178462277HCID 178462277, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of 69 mg of 4-nitrobenzyl (5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-2-yl)-1-carbapen-2-em-3-carboxylate in 2 ml of acetone was added 281 mg of iodoacetamide, and the mixture was stirred at room temperature for 25 hours. The reaction mixture was concentrated under reduced pressure to dryness. The residue was triturated with 3 ml of ethyl acetate, and the insolubles were collected by filtration to give 4-nitrobenzyl (5R,6S)-2-(6-carbamoylmethylimidazo[5,1-b]thiazolium-2-yl)-6-((1R)-1-hydroxyethyl)-1-carbapen-2-em-3-carboxylate iodide.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure to dryness
  2. customThe residue was triturated with 3 ml of ethyl acetate
  3. filtrationthe insolubles were collected by filtration

Sources & evidence

ORD record
ord-f20d953b8dfe40878ea481c904f82f0f
Source dataset
uspto-grants-2001_10
Patent number
US06310056B1

Reaction notes

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