Hydrochloric Acid → HCID 15867801, compound

HRID 1604112Notes

Reaction equation

HRID 1604112 reaction equation
[CH2:1]([C:6]1[CH2:20][C@@H:19]([OH:21])[C@H:18](/[CH:22]=[CH:23]/[C@@H:24]([OH:32])[CH2:25][C@H:26]([CH3:31])[CH2:27][CH2:28][CH2:29][CH3:30])[C:7]=1[S:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16]C)=[O:15])[CH2:2][CH2:3][CH2:4][CH3:5].P([O-])([O-])([O-])=O.Cl.S([O-])([O-])(=O)=O.[NH4+].[NH4+]>CC(C)=O>[CH2:1]([C:6]1[CH2:20][C@@H:19]([OH:21])[C@H:18](/[CH:22]=[CH:23]/[C@@H:24]([OH:32])[CH2:25][C@H:26]([CH3:31])[CH2:27][CH2:28][CH2:29][CH3:30])[C:7]=1[S:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1061PhosphateHCID 6097028Ammonium SulfateHCID 15867800HCID 15867800, compound

Product 1

HCID 15867801HCID 15867801, compoundYield 28.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To methyl (11R,12S,13E,15S,17R)-9-pentyl-11,15-dihydroxy-17,20-dimethyl-7-thiaprosta-8,13-dienoate (20 mg, 0.042 mmol) in acetone (1 mL) was added pH 8 phosphate buffer (5 mL). To this was further added esterase containing solution (derived from pig's liver, made by Sigma Co., 50 μl). The solution was agitated at room temperature for 24 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 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-pentyl-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., 50 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-ca534c053a38497cb302dc00cc9017fe
Source dataset
uspto-grants-1999_11
Patent number
US05990346

Reaction notes

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