Iodoacetamide → HCID 178459451、化合物

HRID 568258ノート

反応式

HRID 568258 の反応式
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]

参加物

5

反応物 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

生成物 1

HCID 178459451HCID 178459451、化合物収率 98.2%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-248c2ed003134a87a029663b4a64bca6
出典データセット
uspto-grants-2001_01
特許番号
US06180622B2

反応ノート

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