Methyl iodide → HCID 178459475, compound

HRID 568215Notes

Reaction equation

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

Participants

Reactant 2

HCID 6328Methyl iodide

HCID 131722292HCID 131722292, compound

Product 1

HCID 178459475HCID 178459475, compoundYield 98.9%

Procedure

Iodomethane (1.00 g) is added to 43.2 mg of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[(imidazo[5,1-b]thiazol-5-yl)methylaminocarbonyl]pyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate, and the mixture is allowed to stand in an argon atmosphere in a light-shielded state at room temperature for 19 hr. The excess reagent is removed by evaporation under reduced pressure to give 52.6 mg of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[(6-methylimidazo[5,1-b]thiazolium-5-yl)methylaminocarbonyl]pyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate iodide as a slightly yellowish solid.

Workup

customThe excess reagent is removed by evaporation under reduced pressure

Sources & evidence

ORD record: ord-d5679ed7feae4d129373c00d26877106
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06180622B2

Reaction notes

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