Iodoacetamide → HCID 178459451, compound

HRID 568258Notes

Reaction equation

HRID 568258 reaction equation
I[CH2:2][C:3]([NH2:5])=[O:4].[Cl:6]([O-])(=O)(=O)=O.[Al+3].Cl([O-])(=O)(=O)=O.Cl([O-])(=O)(=O)=O.[CH2:22]([O:25][C:26]([N:28]1[C@H:32]([CH2:33][C:34]2[S:38][C:37]3=[CH:39][N:40]=[C:41]([Cl:42])[N:36]3[CH:35]=2)[CH2:31][C@H:30]([S:43][C:44]2[C@H:45]([CH3:61])[C@@H:46]3[C@@H:56]([C@H:57]([OH:59])[CH3:58])[C:55](=[O:60])[N:47]3[C:48]=2[C:49]([O:51][CH2:52][CH:53]=[CH2:54])=[O:50])[CH2:29]1)=[O:27])[CH:23]=[CH2:24]>C(#N)C>[Cl-:6].[CH2:22]([O:25][C:26]([N:28]1[C@H:32]([CH2:33][C:34]2[S:38][C:37]3=[CH:39][N:40]([CH2:2][C:3](=[O:4])[NH2:5])[C:41]([Cl:42])=[N+:36]3[CH:35]=2)[CH2:31][C@H:30]([S:43][C:44]2[C@H:45]([CH3:61])[C@@H:46]3[C@@H:56]([C@H:57]([OH:59])[CH3:58])[C:55](=[O:60])[N:47]3[C:48]=2[C:49]([O:51][CH2:52][CH:53]=[CH2:54])=[O:50])[CH2:29]1)=[O:27])[CH:23]=[CH2:24]

Participants

5

Reactant 3

HCID 3727IodoacetamideHCID 159740Aluminum perchlorateHCID 131722367Allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-(5-chloroimidazo[5,1-b]thiazol-2-yl)methylpyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate

Product 1

HCID 178459451HCID 178459451, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Iodoacetamide (198.0 mg) and 221.9 mg of aluminum perchlorate are added to a solution of 42.6 mg of allyl (1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-(5-chloroimidazo[5,1-b]thiazol-2-yl)methylpyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate, described in Example 64-a), in 1.0 ml of dry acetonitrile. The mixture is stirred in an argon atmosphere at room temperature for 48 hr. The mixture is then filtered to remove insolubles, and the filtrate is subjected to evaporation. The residue is purified by column chromatography on Sephadex LH-20 (dichloromethane:methanol=1:1) and then ion-exchanged using Amberlyst A-26 (Cl− form) (water) to give 48.3 mg of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-(6-carbamoylmethyl-5-chloroimidazo[5,1-b]thiazolium-2-yl)methylpyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate chloride as a yellow oil.

Workup

  1. filtrationThe mixture is then filtered
  2. customto remove insolubles
  3. customthe filtrate is subjected to evaporation
  4. customThe residue is purified by column chromatography on Sephadex

Sources & evidence

ORD record
ord-248c2ed003134a87a029663b4a64bca6
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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