Methyl iodide → HCID 178459461, compound

HRID 568238Notes

Reaction equation

HRID 568238 reaction equation
[I:1][CH3:2].[CH2:3]([O:6][C:7]([N:9]1[C@H:13]([CH2:14][C:15]2[N:16]3[CH:22]=[N:21][CH:20]=[C:17]3[S:18][CH:19]=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]3[C:17](=[CH:20][N:21]([CH3:2])[CH:22]=3)[S:18][CH:19]=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]

Participants

3

Reactant 2

HCID 6328Methyl iodideHCID 131722327allyl(1R,5S,6S)-2-[(3S,5R)-1-allyloxycarbonyl-5-(imidazo[5,1-b]thiazol-3-yl)methylpyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate

Product 1

HCID 178459461HCID 178459461, compoundYield 86.5%

Procedure

Iodomethane (2.13 g) is added to 85.0 mg of allyl(1R,5S,6S)-2-[(3S,5R)-1-allyloxycarbonyl-5-(imidazo[5,1-b]thiazol-3-yl)methylpyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate described in Example 20-b), and the mixture is stirred in an argon atmosphere in a light-shielded state at room temperature for 16 hr. 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 91.7 mg of allyl(1R,5S,6S)-2-[(3S,5R)-1-allyloxycarbonyl-5-(6-methylimidazo[5,1-b]thiazolium-3-yl)methylpyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate iodide as a slightly yellow solid.

Workup

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

Sources & evidence

ORD record
ord-71095dfd3ef94123a63c415511665003
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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