Iodoacetamide → HCID 91277219, compound

HRID 1840445Notes

Reaction equation

HRID 1840445 reaction equation
[CH3:1][S:2][C:3]1[N:10]2[C:6]([S:7][C:8]([C:11]3[C@H:12]([CH3:35])[C@@H:13]4[C@@H:30]([C@H:31]([OH:33])[CH3:32])[C:29](=[O:34])[N:14]4[C:15]=3[C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=3)=[O:17])=[CH:9]2)=[C:5]([S:36][CH3:37])[N:4]=1.IC[C:40]([NH2:42])=[O:41]>CC(C)=O>[C:40]([CH2:37][S:36][C:5]1[N:4]=[C:3]([S:2][CH3:1])[N:10]2[CH:9]=[C:8]([C:11]3[C@H:12]([CH3:35])[C@@H:13]4[C@@H:30]([C@H:31]([OH:33])[CH3:32])[C:29](=[O:34])[N:14]4[C:15]=3[C:16]([O:18][CH2:19][C:20]3[CH:21]=[CH:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=3)=[O:17])[S:7][C:6]=12)(=[O:41])[NH2:42]

Participants

4

Reactant 2

HCID 3727IodoacetamideHCID 23388194HCID 23388194, compound

Product 1

HCID 91277219HCID 91277219, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Nitrobenzyl (1S,5R,6S)-2-[5,7-bis(methylthio)imidazo[5,1-b]thiazol-2-yl]-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate (107 mg) was dissolved in 2 ml of acetone. 2-Iodoacetamide (353 mg) was added to the solution. The mixture was stirred at room temperature for 14 days. The solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography on Sephadex LH-20 (chloroform:methanol=1:1) to prepare 88 mg of 4-nitrobenzyl (1S,5R,6S)-2-(7-carbamoylmethylthio-5-methylthioimidazo[5,1-b]thiazol-2-yl)-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate as a crude product.

Workup

  1. customThe solvent was removed by distillation under the reduced pressure
  2. customThe residue was purified by column chromatography on Sephadex
  3. custom(chloroform:methanol=1:1) to prepare 88 mg of 4-nitrobenzyl (1S,5R,6S)-2-(7-carbamoylmethylthio-5-methylthioimidazo[5,1-b]thiazol-2-yl)-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate as a crude product

Sources & evidence

ORD record
ord-c60ab04470274132a4ae77ef805ed351
Source dataset
uspto-grants-2004_01
Patent number
US06680313B2

Reaction notes

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