Réaction #3122

Équation de réaction

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

Rendement 14.0%

Solvants

acetone

Conditions de réaction

Traitement

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

Mode opératoire

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%).

Source