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

HRID 3026

反应方程式

HRID 3026 反应方程式
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]

参与物

6

反应物 4

HCID 313海萝胶HCID 1061无水磷酸二氢钾HCID 6097028C10-16-烷硫酸酯铵盐HCID 22883802Methyl(11R,12S,13E,15S,17S)-9-butyloxy-11,15-dihydroxy-17,20-dimethyl-7-thiaprosta-8,13-dienoate

产物 1

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

试剂、催化剂与溶剂 1

HCID 180丙酮溶剂

实验过程

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%).

后处理

  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)

来源与证据

ORD记录
ord-e22638b8245f48a095b97a9f8f553d18
来源数据集
uspto-grants-1998_03
专利号
US05731452

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