Hydrochloric Acid → Pinellic acid

HRID 227337Notes

Reaction equation

HRID 227337 reaction equation
C([O:5][C:6](=[O:27])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C@H:14]([OH:26])/[CH:15]=[CH:16]/[C@H:17]([OH:25])[C@@H:18]([OH:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])(C)(C)C.[OH-].[K+].Cl>C(O)C.O>[CH3:23][CH2:22][CH2:21][CH2:20][CH2:19][C@H:18]([OH:24])[C@@H:17]([OH:25])/[CH:16]=[CH:15]/[C@@H:14]([OH:26])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:6]([OH:27])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 57756003HCID 57756003, compound

Product 1

HCID 9858729Pinellic acid

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

(9S,12S,13S)-(E)-9,12,13-trihydroxy-10-octadecaenoic acid t-butyl ester (13) (6.5 mg, 0.0168 mmol) was added to an ethanol-water (4:1) solution (500 μL) of 2.0 N potassium hydroxide at room temperature, and the mixture was stirred at room temperature for 46 hours. The reaction solution was cooled to 0° C., 1.0 N hydrochloric acid solution (500 μL) was added to the reaction solution to make it weakly acidic, and the mixture was extracted with chloroform (5 mL) three times. The organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution (5 mL), dried over sodium sulfate, and concentrated. The resulting colorless oily crude product (10 mg) was separated and purified by silica gel column chromatography (chloroform:methanol=10:1) to obtain 9S,12S,13S-trihydroxy-10E-octadecenoic acid (14) as a while solid (4.5 mg, 82%).

Workup

  1. temperatureThe reaction solution was cooled to 0° C.
  2. extractionthe mixture was extracted with chloroform (5 mL) three times
  3. washThe organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution (5 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe resulting colorless oily crude product (10 mg) was separated
  7. custompurified by silica gel column chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-2438b24f40d84bca93b850d786a24927
Source dataset
uspto-grants-2009_07
Patent number
US07560484B2

Reaction notes

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