Iodoacetamide → allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[6-(carbamoylmethyl)imidazo[5,1-b]thiazolium-2-yl]methylpyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate iodide

HRID 568243Notes

Reaction equation

HRID 568243 reaction equation
[I:1][CH2:2][C:3]([NH2:5])=[O:4].[CH2:6]([O:9][C:10]([N:12]1[C@H:16]([CH2:17][C:18]2[S:22][C:21]3=[CH:23][N:24]=[CH:25][N:20]3[CH:19]=2)[CH2:15][C@H:14]([S:26][C:27]2[C@H:28]([CH3:44])[C@@H:29]3[C@@H:39]([C@H:40]([OH:42])[CH3:41])[C:38](=[O:43])[N:30]3[C:31]=2[C:32]([O:34][CH2:35][CH:36]=[CH2:37])=[O:33])[CH2:13]1)=[O:11])[CH:7]=[CH2:8]>CC(C)=O>[I-:1].[CH2:6]([O:9][C:10]([N:12]1[C@H:16]([CH2:17][C:18]2[S:22][C:21]3=[CH:23][N:24]([CH2:2][C:3](=[O:4])[NH2:5])[CH:25]=[N+:20]3[CH:19]=2)[CH2:15][C@H:14]([S:26][C:27]2[C@H:28]([CH3:44])[C@@H:29]3[C@@H:39]([C@H:40]([OH:42])[CH3:41])[C:38](=[O:43])[N:30]3[C:31]=2[C:32]([O:34][CH2:35][CH:36]=[CH2:37])=[O:33])[CH2:13]1)=[O:11])[CH:7]=[CH2:8]

Participants

4

Reactant 2

HCID 3727IodoacetamideHCID 131722333HCID 131722333, compound

Product 1

HCID 178459459allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[6-(carbamoylmethyl)imidazo[5,1-b]thiazolium-2-yl]methylpyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate iodideYield 76.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Iodoacetamide (96.1 mg) is added to a solution of 33.9 mg of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-(imidazo[5,1-b]thiazol-2-yl)methylpyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate described in Example 23-a) in 0.5 ml of dry acetone, and the mixture is stirred in an argon atmosphere at room temperature for 20 hr. The solvent is removed by evaporation under reduced pressure, and the residue is purified by column chromatography on Sephadex LH-20 (dichloromethane:methanol=1:1) to give 34.5 mg of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[6-(carbamoylmethyl)imidazo[5,1-b]thiazolium-2-yl]methylpyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate iodide as a slightly yellow solid.

Workup

  1. customThe solvent is removed by evaporation under reduced pressure
  2. customthe residue is purified by column chromatography on Sephadex

Sources & evidence

ORD record
ord-6c4f8ac4058348a2a3e7fa9aadcac3b6
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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