Reaktion #3122

Reaktionsgleichung

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

Ausbeute 14.0%

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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%).

Quelle