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

HRID 3026

반응식

HRID 3026 반응식
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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-e22638b8245f48a095b97a9f8f553d18
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05731452

연결된 노트

불러오는 중…