Hydrochloric Acid → HCID 56632227, compound

HRID 1789616Notes

Reaction equation

HRID 1789616 reaction equation
P([O-])([O-])([O-])=O.[Cl:6][C:7]1[C:8](=[O:30])[C:9](=[CH:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25](=[C:28]=[O:29])OC)[C@H:10]([CH:12]=[CH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH:11]=1.Cl.S([O-])([O-])(=O)=[O:33].[NH4+].[NH4+]>CC(C)=O>[Cl:6][C:7]1[C:8](=[O:30])[C:9](=[CH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:28]([OH:29])=[O:33])[C@H:10]([CH:12]=[CH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1061PhosphateHCID 6097028Ammonium SulfateHCID 86741759HCID 86741759, compound

Product 1

HCID 56632227HCID 56632227, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

450 ml of 0.1M phosphate buffer (pH8) was added to a solution of 734 mg (2.0 mmol) of (4R)-2-chloro-4-(1-octenyl)-5-(6-methoxy-carbonylhexylidene)-2-cyclopentenone in 45 ml of acetone, and then 45 ml of an aqueous solution of pig liver esterase was added. The mixture was stirred at 30°-35° C. for 100 hours. 0.1N hydrochloric acid was added to the reaction mixture to adjust its pH to 4, and then the mixture was saturated with ammonium sulfate. It was filtered, and then extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The dried product was filtered, concentrated and subjected to silica gel column chromatography (silica gel, 50 mg; eluent, hexane:acetone:acetic acid=10:2:0.05→5:2:0.003) to give 480 mg (yield 68%) of (4R)-2-chloro-4-(1-octenyl)-5-(6-carboxyhexylidene)-2-cyclopentenone.

Workup

  1. filtrationIt was filtered
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe dried product was filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9b485789b41c43dd8117545ba68b1c3a
Source dataset
uspto-grants-1987_08
Patent number
US04689426

Reaction notes

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