Hydrochloric Acid → HCID 15867818, compound

HRID 1604122Notes

Reaction equation

HRID 1604122 reaction equation
[OH:1][C@H:2]1[C@H:16](/[CH:17]=[CH:18]/[C@@H:19]([OH:27])[CH2:20][C@H:21]([CH3:26])[CH2:22][CH2:23][CH2:24][CH3:25])[C:5]([S:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14]C)=[O:13])=[CH:4][CH2:3]1.P([O-])([O-])([O-])=O.Cl.S([O-])([O-])(=O)=O.[NH4+].[NH4+]>CC(C)=O>[OH:1][C@H:2]1[C@H:16](/[CH:17]=[CH:18]/[C@@H:19]([OH:27])[CH2:20][C@H:21]([CH3:26])[CH2:22][CH2:23][CH2:24][CH3:25])[C:5]([S:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:4][CH2:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1061PhosphateHCID 6097028Ammonium SulfateHCID 15867817HCID 15867817, compound

Product 1

HCID 15867818HCID 15867818, compoundYield 12.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To methyl (11R,12S,13E,15S,17R)-11,15-dihydroxy-17,20-dimethyl-7-thiaprosta-8,13-dienoate (37.2 mg, 0.093 mmol) in acetone (1 mL) was added pH 8 phosphate buffer (10 mL). To this was further added esterase containing solution (derived from pig's liver, made by Sigma Co., 100 μl). This was agitated at room temperature for 15 hours. Dilute hydrochloric acid was added to the reaction solution to make the solution pH 4. Further, The solution was made saturated by ammonium sulfate, then the target produce was extracted with ethyl acetate. The extract was washed with brine, then was dried over anhydrous sodium sulfate. The solution was concentrated under reduced pressure, then subjected to thin layer chromatography for separation (development solution: ethyl acetate) to obtain (11R,12S,13E,15S,17R)-11,15-dihydroxy-17,20-dimethyl-7-thiaprosta-8,13-dienoic acid (4.6 mg, 12%).

Workup

  1. additioncontaining solution (derived from pig's liver, made by Sigma Co., 100 μl)
  2. customthe target produce
  3. extractionwas extracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. concentrationThe solution was concentrated under reduced pressure
  7. customsubjected to thin layer chromatography for separation (development solution: ethyl acetate)

Sources & evidence

ORD record
ord-f41568e80c9043939e1c0a48236f93c3
Source dataset
uspto-grants-1999_11
Patent number
US05990346

Reaction notes

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