Реакция #655403

Уравнение реакции

Acetic acid

tetra-n-butyl ammonium fluoride THF

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-(t-butyldimethylsilyloxy)ethyl]-1-methylcarbapen-2-em-3-carboxylate

→

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

Выход 66.8%

Растворители

THF

ethyl acetate

Условия реакции

Обработка

1. 1
   Промывкаthe diluted solution is successively washed with 40 ml of a 1/15 M phosphate buffer (pH 7.0) and 20 ml of saturated saline
2. 2
   Сушкаthe washed solution is dried over anhydrous magnesium sulfate
3. 3
   Фильтрацияfiltered
4. 4
   Другоеthe solvent is removed by evaporation
5. 5
   Другоеto give 193 mg of a slightly yellow oil
6. 6
   ДругоеThis oil is successively purified by column chromatography on silica gel (ethyl acetate:methanol=95:5→9:1) and on Sephadex

Методика

Acetic acid (0.26 ml) and 1.52 ml of a 1 M tetra-n-butyl ammonium fluoride/THF solution are added to a solution of 213 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-(t-butyldimethylsilyloxy)ethyl]-1-methylcarbapen-2-em-3-carboxylate (stereoisomer B) in 4.5 ml of anhydrous THF, and the mixture is stirred in an argon atmosphere at room temperature for 38 hr. The reaction solution is diluted with 80 ml of ethyl acetate, the diluted solution is successively washed with 40 ml of a 1/15 M phosphate buffer (pH 7.0) and 20 ml of saturated saline, the washed solution is dried over anhydrous magnesium sulfate and filtered, and the solvent is removed by evaporation to give 193 mg of a slightly yellow oil. This oil is successively purified by column chromatography on silica gel (ethyl acetate:methanol=95:5→9:1) and on Sephadex LH-20 (chloroform:methanol=1:1) to give 119.2 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) as a milky white amorphous material.

Источник