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

HRID 3026

Reaktionsgleichung

Reaktionsgleichung von HRID 3026
C[O:2][C:3](=[O:32])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][S:9][C:10]1[C@@H:14](/[CH:15]=[CH:16]/[C@@H:17]([OH:25])[CH2:18][C@@H:19]([CH3:24])[CH2:20][CH2:21][CH2:22][CH3:23])[C@H:13]([OH:26])[CH2:12][C:11]=1[O:27][CH2:28][CH2:29][CH2:30][CH3:31].P([O-])([O-])([O-])=O.Cl.S([O-])([O-])(=O)=O.[NH4+].[NH4+]>CC(C)=O>[CH2:28]([O:27][C:11]1[CH2:12][C@@H:13]([OH:26])[C@H:14](/[CH:15]=[CH:16]/[C@@H:17]([OH:25])[CH2:18][C@@H:19]([CH3:24])[CH2:20][CH2:21][CH2:22][CH3:23])[C:10]=1[S:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:32])=[O:2])[CH2:29][CH2:30][CH3:31]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 1061PhosphateHCID 6097028Ammonium SulfateHCID 22883802Methyl(11R,12S,13E,15S,17S)-9-butyloxy-11,15-dihydroxy-17,20-dimethyl-7-thiaprosta-8,13-dienoate

Produkt 1

HCID 22883777(11R,12S,13E,15S,17S)-9-butyloxy-11,15-dihydroxy-17,20-dimethyl-7-thiaprosta-8,13-dienoic acidAusbeute 14 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  1. additionFurther esterase (from porcine liver made by Sigma Co., 114 μl) was added
  2. temperaturecooled
  3. extractionThe mixture was extracted by ethyl acetate
  4. customthe extract was dried
  5. concentrationwas concentrated under reduced pressure
  6. customThe concentrate was purified by thin layer chromatography (developing solvent: ethyl acetate, Rf=0.2)

Quellen und Nachweise

ORD-Eintrag
ord-e22638b8245f48a095b97a9f8f553d18
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05731452

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