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 568252ノート

反応式

HRID 568252 の反応式
[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]

参加物

4

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-0a43aa252819443da69cf841205b85a7
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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