Iodomethyl methyl ether → allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[6-methoxymethyl-5-methylimidazo[5,1-b]thiazolium-2-yl]methylpyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate iodide

HRID 568252노트

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HRID 568252 반응식
[CH3:1][O:2][CH2:3][I:4].[CH2:5]([O:8][C:9]([N:11]1[C@H:15]([CH2:16][C:17]2[S:21][C:20]3=[CH:22][N:23]=[C:24]([CH3:25])[N:19]3[CH:18]=2)[CH2:14][C@H:13]([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])[CH2:12]1)=[O:10])[CH:6]=[CH2:7]>CC(C)=O>[I-:4].[CH2:5]([O:8][C:9]([N:11]1[C@H:15]([CH2:16][C:17]2[S:21][C:20]3=[CH:22][N:23]([CH2:1][O:2][CH3:3])[C:24]([CH3:25])=[N+:19]3[CH:18]=2)[CH2:14][C@H:13]([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])[CH2:12]1)=[O:10])[CH:6]=[CH2:7]

참가 물질

4

반응물 2

HCID 139376Iodomethyl methyl etherHCID 131722343Allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-(5-methylimidazo[5,1-b]thiazol-2-yl)methylpyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate

생성물 1

HCID 178459456allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[6-methoxymethyl-5-methylimidazo[5,1-b]thiazolium-2-yl]methylpyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate iodide

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

Iodomethyl methyl ether (0.01 ml) is added to a solution of 34.0 mg of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-(5-methylimidazo[5,1-b]thiazol-2-yl)methylpyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate, described in Example 31-a), in 0.5 ml of dry acetone, and the mixture is stirred in an argon atmosphere at room temperature for 10 min. The solvent is removed by evaporation under reduced pressure. The residue is purified by column chromatography on Sephadex LH-20 (dichloromethane:methanol=1:1) to give 42.3 mg of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[6-methoxymethyl-5-methylimidazo[5,1-b]thiazolium-2-yl]methylpyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate iodide as a yellow oil.

후처리

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

출처 및 근거

ORD 기록
ord-0a43aa252819443da69cf841205b85a7
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06180622B2

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