Реакция #655404

Уравнение реакции

water

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

N-methylaniline

monochlorobenzene

→

colorless flocculent material

Выход 45.0%

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

Выход 45.0%

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) (12.7 mg) is added to a solution of 64.8 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) and 0.072 ml of N-methylaniline in a mixture of 0.9 ml of dry dichloromethane with 0.9 ml of monochlorobenzene, and the mixture is stirred in an argon atmosphere at room temperature for 70 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 23 mg of a colorless flocculent material. The colorless flocculent material is successively purified by column chromatography on Diaion CHP-20P (4% aqueous THF solution) and on Cosmosil 5C18-MS (water:methanol=2:1) to give 5.8 mg of the title compound as a colorless flocculent material.

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