Реакция #655405

Уравнение реакции

Iodomethane

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

→

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

Выход 97.4%

Условия реакции

Обработка

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

Методика

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.

Источник