Methyl iodide → HCID 178459463, compound

HRID 568226Notes

Reaction equation

[I:1][CH3:2].[CH2:3]([O:6][C:7]([N:9]1[C@H:13]([CH2:14][C:15]2[N:22]3[C:18]([S:19][CH:20]=[CH:21]3)=[CH:17][N:16]=2)[CH2:12][C@H:11]([S:23][C:24]2[C@H:25]([CH3:41])[C@@H:26]3[C@@H:36]([C@H:37]([OH:39])[CH3:38])[C:35](=[O:40])[N:27]3[C:28]=2[C:29]([O:31][CH2:32][CH:33]=[CH2:34])=[O:30])[CH2:10]1)=[O:8])[CH:4]=[CH2:5]>>[I-:1].[CH2:3]([O:6][C:7]([N:9]1[C@H:13]([CH2:14][C:15]2[N:16]([CH3:2])[CH:17]=[C:18]3[N+:22]=2[CH:21]=[CH:20][S:19]3)[CH2:12][C@H:11]([S:23][C:24]2[C@H:25]([CH3:41])[C@@H:26]3[C@@H:36]([C@H:37]([OH:39])[CH3:38])[C:35](=[O:40])[N:27]3[C:28]=2[C:29]([O:31][CH2:32][CH:33]=[CH2:34])=[O:30])[CH2:10]1)=[O:8])[CH:4]=[CH2:5]

Participants

Reactant 2

HCID 6328Methyl iodide

HCID 131722308HCID 131722308, compound

Product 1

HCID 178459463HCID 178459463, compoundYield 93.3%

Procedure

Iodomethane (0.71 g) is added to 57.2 mg of allyl(1R,5S,6S)-2-[(3S,5R)-1-allyloxycarbonyl-5-(imidazo[5,1-b]thiazol-5-yl)methylpyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate, and the mixture is stirred in an argon atmosphere in a light-shielded state at room temperature for 3 days. The excess reagent is removed by evaporation under reduced pressure, and the residue is purified by column chromatography on Sephadex LH-20 (dichloromethane methanol=1:1) to give 66.6 mg of allyl(1R,5S,6S)-2-[(3S,5R)-1-allyloxycarbonyl-5-(6-methylimidazo[5,1-b]thiazolium-5-yl)methylpyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate iodide as a yellow brown powder.

Workup

customThe excess reagent is removed by evaporation under reduced pressure
customthe residue is purified by column chromatography on Sephadex

Sources & evidence

ORD record: ord-fb9da896de764f0ba11641bd98d11259
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06180622B2

Reaction notes

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