Hydrochloric Acid → 2-Methylthio-5-(6-carboxyhexylidene)-4-(3-hydroxy-1-octenyl)-2-cyclopentenone

HRID 1197046Notes

Reaction equation

HRID 1197046 reaction equation
[CH3:1][S:2][C:3]1[C:4](=[O:27])[C:5](=[CH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25]C)=[O:24])[CH:6]([CH:8]=[CH:9][CH:10]([OH:16])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:7]=1.P([O-])([O-])([O-])=O.Cl.S([O-])([O-])(=O)=O.[NH4+].[NH4+]>CC(C)=O.C(OCC)(=O)C>[CH3:1][S:2][C:3]1[C:4](=[O:27])[C:5](=[CH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[CH:6]([CH:8]=[CH:9][CH:10]([OH:16])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1061PhosphateHCID 6097028Ammonium SulfateHCID 56608063HCID 56608063, compound

Product 1

HCID 571118542-Methylthio-5-(6-carboxyhexylidene)-4-(3-hydroxy-1-octenyl)-2-cyclopentenoneYield 58%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 345 mg of 2-methylthio-5-(6-methoxycarbonylhexylidene)-4-(3-hydroxy-1-octenyl)-2-cyclopentenone obtained in Example 34 dissolved in 20 ml of acetone was added 220 ml of 0.1M phosphate buffer of pH 8. While the mixture was stirred, 24 mg of pig liver esterase was added thereto, and the mixture was stirred at 30-35° C. for 150 hours. After the pH was adjusted to 4 with 0.1N hydrochloric acid, ammonium sulfate was added to saturation and ethyl acetate was added, followed by filtration. The filtrate was extracted with ethyl acetate, and the organic layers were combined and washed with saturated aqueous sodium chloride. The product was dried over anhydrous magnesium sulfate, filtered and concentrated, followed by silica gel chromatography to give 193 mg (yield 58%) of 2-methylthio-5-(6-carboxyhexylidene)-4-(3-hydroxy-1-octenyl)-2-cyclopentenone.

Workup

  1. addition24 mg of pig liver esterase was added
  2. stirringthe mixture was stirred at 30-35° C. for 150 hours
  3. additionwas added
  4. filtrationfollowed by filtration
  5. extractionThe filtrate was extracted with ethyl acetate
  6. washwashed with saturated aqueous sodium chloride
  7. dry with materialThe product was dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-adec0ab354ad454baedb6ae74fe4392a
Source dataset
uspto-grants-1992_05
Patent number
US05116869

Reaction notes

Loading…