Hydrochloric Acid → HCID 54263751, compound

HRID 1197067Notes

Reaction equation

HRID 1197067 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])[C:6]([OH:16])([CH2:8][CH2:9][CH2:10][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>[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])[C:6]([OH:16])([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1061PhosphateHCID 6097028Ammonium SulfateHCID 54026159HCID 54026159, compound

Product 1

HCID 54263751HCID 54263751, compoundYield 49.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 16 mg of 2-methylthio-4-hydroxy-5-(6-methoxycarbonylhexylidene)-4-octyl-2-cyclopentenone obtained in Example 101, dissolved in 1 ml of acetone, 11 ml of 0.1M phosphate buffer of pH 8 was added. Under stirring, 1.5 mg of pig liver esterase was added, and the mixture was stirred at 30-35° C. for 130 hours. After the mixture was adjusted to pH 4 with 0.1N hydrochloric acid, ammonium sulfate was added to saturation and the mixture was filtered with addition of ethyl acetate. The filtrate was extracted with ethyl acetate, the organic layers were combined and washed with saturated aqueous sodium chloride. After drying over anhydrous magnesium sulfate, filtration and concentration, the concentrate was subjected to silica gel column chromatography to give 7.7 mg (yield 47%) of 2-methylthio-5-(6-carboxyhexylidene)-4-hydroxy-4-octyl-2-cyclopentenone.

Workup

  1. addition1.5 mg of pig liver esterase was added
  2. stirringthe mixture was stirred at 30-35° C. for 130 hours
  3. additionwas added to saturation
  4. filtrationthe mixture was filtered with addition of ethyl acetate
  5. extractionThe filtrate was extracted with ethyl acetate
  6. washwashed with saturated aqueous sodium chloride
  7. dry with materialAfter drying over anhydrous magnesium sulfate, filtration and concentration

Sources & evidence

ORD record
ord-887753a9b34240c4b31feb97896ed586
Source dataset
uspto-grants-1992_05
Patent number
US05116869

Reaction notes

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