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

HRID 3026

反応式

HRID 3026 の反応式
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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-e22638b8245f48a095b97a9f8f553d18
出典データセット
uspto-grants-1998_03
特許番号
US05731452

関連ノート

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