Hydrochloric Acid → HCID 15480017, compound

HRID 1873237Notes

Reaction equation

HRID 1873237 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]([OH:28])(=[O:27])[C:20]1[C:21](=[CH:23][CH:24]=[CH:25][CH:26]=1)[SH:22].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:22][C:21]1[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=1[C:19]([OH:28])=[O:27])([OH:5])=[O:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 54432-Mercaptobenzoic AcidHCID 14797Potassium HydroxideHCID 15480018HCID 15480018, compound

Product 1

HCID 15480017HCID 15480017, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 21901998Ethyl acetate hexane acetic acidSolvent

Conditions

Temperature
100 °C

Procedure

0.2 M Aqueous potassium hydroxide solution (5 mL, oxygen was removed by addition of 15 mg of sodium hydrosulfite in advance) was mixed with 2-(3-carboxymethyl-4-iodophenyl)propionic acid (prepared in Example 12, 40.7 mg, 0.122 mmol.) and thiosalicylic acid (37.3 mg, 0.242 mmol.). The resulting mixture was heated for 20 hours under reflux (temperature: approx. 100° C.) after addition of 10 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 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 40.6 mg (0.084 mmol., yield: 69%) of the desired compound.

Workup

  1. temperatureThe resulting mixture was heated for 20 hours
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate portion was washed with an aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customto leave a residue

Sources & evidence

ORD record
ord-ec9113a3c1c0408ba06478c2027120b9
Source dataset
uspto-grants-2000_08
Patent number
US06111115

Reaction notes

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