Lithium Hydroxide → HCID 22457717, compound

Participants

Reaction Steps

A solution of ethyl 3-({2-[(4-fluorophenyl)carbonylamino]ethylthio}methyl)-4-oxo-4-(3-pyridyl)butanoate (100 mg) and lithium hydroxide (1 eq) was stirred a temperature in ethanol-water (1:1, 2 mL) till the starting material disappeared. The solution was acidified and purified on preparative HPLC (C-18 prep column, 10% to 90% acetonitrile in water both containing 0.1% TFA) to give 91 mg of 3-({2-[(4-fluorophenyl)carbonylamino]ethylthio}methyl)-4-oxo-4-(3-pyridyl)butanoic acid. The acid (91 mg) was treated with ethyl chloroformate (1.1 eq) and triethylamine (1.1 eq) in tetrahydrofuran (2.5 mL) at room temperature for 10 minutes. Piperidine (1.1 eq) was added to the reaction mixture and stirred at room temperature overnight. The solution was concentrated and purified on preparative HPLC (C-18 prep column, 10% to 90% acetonitrile in water both containing 0.1% TFA) to give 66 mg of the title compound; ESMS (M+1)+458.

Provenance & Evidence