Iodoacetamide → HCID 178459451, 화합물

HRID 568258노트

반응식

HRID 568258 반응식
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]

참가 물질

5

반응물 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

생성물 1

HCID 178459451HCID 178459451, 화합물수율 98.2%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-248c2ed003134a87a029663b4a64bca6
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06180622B2

반응 노트

불러오는 중…