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 568252Notes

Reaction equation

HRID 568252 reaction equation
[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]

Participants

4

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-0a43aa252819443da69cf841205b85a7
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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