Methyl iodide → HCID 178459472, compound

HRID 568223Notes

Reaction equation

HRID 568223 reaction equation
[I:1][CH3:2].[CH2:3]([O:6][C:7]([N:9]1[C@H:13]([CH:14]([OH:23])[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:24][C:25]2[C@H:26]([CH3:42])[C@@H:27]3[C@@H:37]([C@H:38]([OH:40])[CH3:39])[C:36](=[O:41])[N:28]3[C:29]=2[C:30]([O:32][CH2:33][CH:34]=[CH2:35])=[O:31])[CH2:10]1)=[O:8])[CH:4]=[CH2:5]>>[I-:1].[CH2:3]([O:6][C:7]([N:9]1[C@H:13]([CH:14]([OH:23])[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:24][C:25]2[C@H:26]([CH3:42])[C@@H:27]3[C@@H:37]([C@H:38]([OH:40])[CH3:39])[C:36](=[O:41])[N:28]3[C:29]=2[C:30]([O:32][CH2:33][CH:34]=[CH2:35])=[O:31])[CH2:10]1)=[O:8])[CH:4]=[CH2:5]

Participants

3

Reactant 2

HCID 6328Methyl iodideHCID 131722300HCID 131722300, compound

Product 1

HCID 178459472HCID 178459472, compoundYield 97.4%

Procedure

Iodomethane (0.71 g) is added to 58.8 mg of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-3-yl)methyl]pyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate (stereoisomer B) described in Example 8-b), and the mixture is stirred in an argon atmosphere in a light-shielded state at room temperature for 24 hr. The excess reagent is removed by evaporation under reduced pressure, and the residue is purified by column chromatography on Sephadex LH-20 (chloroform:methanol=1:1) to give 71.1 mg of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[1-hydroxy-1-(6-methylimidazo[5,1-b]thiazolium-3-yl)methyl]pyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate iodide (stereoisomer B) as a light brown oil. Silver perchlorate (31 mg) is added to a solution of this oil in a mixture of 2 ml of dry dichloromethane with 2 ml of acetonitrile, and the mixture is stirred. The solvent is removed by evaporation, and acetonitrile is again added for suspension, followed by filtration and the removal of the solvent by evaporation to give an oil. The oil is then purified by column chromatography on Sephadex LH-20 (chloroform:methanol=1:1) to give 55 mg of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[1-hydroxy-1-(6-methylimidazo[5,1-b]thiazolium-3-yl)methyl]pyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate perchlorate (stereoisomer B) as a light brown amorphous material.

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-f714d291dd4f4f04946352dac5171dab
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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