Potassium Hydroxide → HCID 22389490, compound

Participants

Reaction Conditions

Reaction Steps

A solution of {3-[3-cyclopentyl-2-(3,4-dichloro-phenyl)-propionyl]-ureido}-acetic acid ethyl ester (prepared in Example 12B-d, 77 mg, 0.19 mmol) in ethanol (5 mL) at 25° C. was treated with a solution of potassium hydroxide (36 mg, 0.65 mmol) in water (1 mL). The reaction mixture was stirred at 25° C. for 2 h. At this time, the reaction was diluted with water (5 mL) and the ethanol was removed in vacuo. The aqueous layer was then acidified to pH=2 with a 1N aqueous hydrochloric acid solution and extracted with methylene chloride (3×15 mL). The organics were then dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 88/12 chloroform/methanol plus 1% acetic acid) afforded {3-[3-cyclopentyl-2-(3,4-dichloro-phenyl)-propionyl]-ureido}-acetic acid (43 mg, 60%) as a white solid: mp 204.2-206.8° C.; EI-HRMS m/e calcd for C17H20Cl2N2O4 (M+) 386.0800, found 386.0795.

Provenance & Evidence