Реакция #3122

Уравнение реакции

hydrochloric acid

Methyl(11R,12S,13E,15S,17S)-9-butyloxy-11,15-dihydroxy-17,20-dimethyl-7-thiaprosta-8,13-dienoate

phosphate

ammonium sulfate

→

(11R,12S,13E,15S,17S)-9-butyloxy-11,15-dihydroxy-17,20-dimethyl-7-thiaprosta-8,13-dienoic acid

Выход 14.0%

Растворители

acetone

Условия реакции

Обработка

1. 1
   workup.ADDITIONFurther esterase (from porcine liver made by Sigma Co., 114 μl) was added
2. 2
   Температураcooled
3. 3
   ЭкстракцияThe mixture was extracted by ethyl acetate
4. 4
   Другоеthe extract was dried
5. 5
   Концентрированиеwas concentrated under reduced pressure
6. 6
   ДругоеThe concentrate was purified by thin layer chromatography (developing solvent: ethyl acetate, Rf=0.2)

Методика

Methyl(11R,12S,13E,15S,17S)-9-butyloxy-11,15-dihydroxy-17,20-dimethyl-7-thiaprosta-8,13-dienoate (51 mg, 0.11 mmol) was dissolved in acetone (1 ml). To this solution was added a pH 8 phosphate buffer (10 ml). Further esterase (from porcine liver made by Sigma Co., 114 μl) was added and the mixture was stirred at room temperature for five hours. Further in a state with methyl ester remaining, the reaction solution was ice cooled, was made pH 4 by dilute hydrochloric acid, and was saturated by ammonium sulfate. The mixture was extracted by ethyl acetate, the extract was dried, then was concentrated under reduced pressure. The concentrate was purified by thin layer chromatography (developing solvent: ethyl acetate, Rf=0.2) to obtain (11R,12S,13E,15S,17S)-9-butyloxy-11,15-dihydroxy-17,20-dimethyl-7-thiaprosta-8,13-dienoic acid (7 mg, 14%).

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