Реакция #655406

Уравнение реакции

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

N-methylaniline

water

→

light orange flocculent material

Выход 68.4%

(1R,5S,6S)-6-((1R)-1-Hydroxyethyl)-2-[(3S,5S)-5-[1-hydroxy-1-(6-methylimidazo[5,1-b]thiazolium-3-yl)methyl]pyrrolidin-3-yl]thio-1-methylcarbapen-2-em-3-carboxylic acid perchlorate

Выход 68.4%

Растворители

dichloromethane

Условия реакции

Обработка

1. 1
   Промывкаthe mixture is washed three times with 3 ml of ethyl acetate
2. 2
   Фильтрацияthe aqueous layer is filtered
3. 3
   Концентрированиеfollowed by concentration under reduced pressure and freeze
4. 4
   Другоеdrying

Методика

Tetrakis(triphenylphosphine)palladium(0) (18.1 mg) is added to a solution of 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) and 0.051 ml of N-methylaniline in 0.7 ml of dry dichloromethane, and the mixture is stirred in an argon atmosphere at room temperature for 45 min. Distilled water (3 ml) is added thereto, the mixture is washed three times with 3 ml of ethyl acetate, and the aqueous layer is filtered, followed by concentration under reduced pressure and freeze drying to give 31 mg of a light orange flocculent material. The light orange flocculent material is purified by column chromatography on Cosmosil 5C18-MS (water:methanol=10:1) to give 3.9 mg of the title compound as a colorless flocculent material.

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