Hydrochloric Acid → HCID 9883399, compound

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence