Hydrochloric Acid → HCID 15867798, compound

HRID 1604109Notes

Reaction equation

HRID 1604109 reaction equation
[CH3:1][C:2]1[CH2:16][C@@H:15]([OH:17])[C@H:14](/[CH:18]=[CH:19]/[C@@H:20]([OH:28])[CH2:21][C@H:22]([CH3:27])[CH2:23][CH2:24][CH2:25][CH3:26])[C:3]=1[S:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12]C)=[O:11].P([O-])([O-])([O-])=O.Cl.S([O-])([O-])(=O)=O.[NH4+].[NH4+]>CC(C)=O>[CH3:1][C:2]1[CH2:16][C@@H:15]([OH:17])[C@H:14](/[CH:18]=[CH:19]/[C@@H:20]([OH:28])[CH2:21][C@H:22]([CH3:27])[CH2:23][CH2:24][CH2:25][CH3:26])[C:3]=1[S:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1061PhosphateHCID 6097028Ammonium SulfateHCID 15867788HCID 15867788, compound

Product 1

HCID 15867798HCID 15867798, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To methyl (11R,12S,13E,15S,17R)-9-methyl-11,15-dihydroxy-17,20-dimethyl-7-thiaprosta-8,13-dienoate (41 mg, 0.099 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. To the reaction solution was added dilute hydrochloric acid to make the solution pH 4. Further, the solution was made saturated by ammonium sulfate, then the desired product 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 chromotography for separation (development solution: ethyl acetate) to obtain (11R,12S,13E,15S,17R)-9-methyl-11,15-dihydroxy-17,20-dimethyl-7-thiaprosta-8,13-dienoic acid (5.4 mg, 14%).

Workup

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

Sources & evidence

ORD record
ord-e76f3cae197343309440b9db5db23218
Source dataset
uspto-grants-1999_11
Patent number
US05990346

Reaction notes

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