Hydrochloric Acid → HCID 59529472, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4-[(cyclohexyl{2-methyl-5-[4-(trifluoromethyl)phenyl]thiophen-3-yl}methyl)amino]benzoic acid (300 mg) synthesized in Example 280 (4), methyl 3-amino-2-hydroxypropanoate hydrochloride (118 mg), 1-hydroxybenzotriazole monohydrate (117 mg) and triethylamine (106 μL) in N,N-dimethylformamide (10 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (146 mg), and the mixture was stirred at 50° C. for 1 hr. 1N Hydrochloric acid was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (70% ethyl acetate/hexane) to give colorless oil. To a mixture of the obtained oil, tetrahydrofuran (5 mL) and ethanol (5 mL) was added 1N aqueous sodium hydroxide solution (1 mL), and the mixture was stirred at room temperature overnight, and concentrated under reduced pressure. The residue was dissolved in water (10 mL), 1N hydrochloric acid (1 mL) was added at 0° C., and the resulting precipitate was collected by filtration to give a white solid. The obtained solid was dissolved in ethyl acetate, dried over magnesium sulfate, and concentrated under reduced pressure to give the title compound (190 mg, 53%) as a white solid.

Provenance & Evidence