Hydrochloric Acid → HCID 9883399, compound

HRID 1873233Notes

Reaction equation

HRID 1873233 reaction equation
[OH-].[K+].[C:3]([CH2:6][C:7]1[CH:8]=[C:9]([CH:14]([CH3:18])[C:15]([OH:17])=[O:16])[CH:10]=[CH:11][C:12]=1I)([OH:5])=[O:4].[C:19]1([SH:25])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>[Cu].CCCCCC.C(OCC)(=O)C.C(O)(=O)C>[C:3]([CH2:6][C:7]1[CH:8]=[C:9]([CH:14]([CH3:18])[C:15]([OH:17])=[O:16])[CH:10]=[CH:11][C:12]=1[S:25][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([OH:5])=[O:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7969ThiophenolHCID 14797Potassium HydroxideHCID 15480018HCID 15480018, compound

Product 1

HCID 9883399HCID 9883399, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 21901998Ethyl acetate hexane acetic acidSolvent

Conditions

Temperature
100 °C

Procedure

0.3 M Aqueous potassium hydroxide solution (10 mL, oxygen was removed by addition of 20 mg of sodium hydrosulfite in advance) was mixed with 2-(3-carboxymethyl-4-iodophenyl)propionic acid (prepared in the manner as described in Example 12, 203 mg, 0.607 mmol.) and thiophenol (95 wt. %, 94 mg, 0.81 mmol.). The resulting mixture was heated for 19 hours under reflux (temperature: approx. 100° C.) after addition of 20 mg of powdery copper. The reaction mixture was cooled, made acidic by addition of hydrochloric acid, and extracted with ethyl acetate. The ethyl acetate portion was extracted with an aqueous saturated sodium hydrogen carbonate solution. The aqueous portion was washed with ethyl acetate, made acidic by addition of hydrochloric acid, and extracted with ethyl acetate. The ethyl acetate portion was washed with an aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated to leave a residue. The residue was subjected to silica gel column chromatography (Wako Gel C-200, Wako Jyunyaku Industry Co., Ltd., hexane/ethyl acetate/acetic acid=7/3/1, v/v/v) to obtain 133 mg (0.420 mmol., yield: 69%) of the desired compound.

Workup

  1. customprepared in the manner
  2. temperatureThe resulting mixture was heated for 19 hours
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with ethyl acetate
  5. extractionThe ethyl acetate portion was extracted with an aqueous saturated sodium hydrogen carbonate solution
  6. washThe aqueous portion was washed with ethyl acetate
  7. additionmade acidic by addition of hydrochloric acid
  8. extractionextracted with ethyl acetate
  9. washThe ethyl acetate portion was washed with an aqueous sodium chloride solution
  10. dry with materialdried over magnesium sulfate
  11. concentrationconcentrated
  12. customto leave a residue

Sources & evidence

ORD record
ord-b8287944be8b4a71a74b3bf84f440bba
Source dataset
uspto-grants-2000_08
Patent number
US06111115

Reaction notes

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