Water → (E)-(2S,3S)-3-[(S)-2-(4-butoxy-phenyl)-1-carboxy-ethylcarbamoyl]-12,12-difluoro-2-hydroxy-2-(2-methoxy-ethyl)-nonadec-4-enoic acid

Participants

Reaction Conditions

Reaction Steps

(E)-(2S,3S)-3-[(S)-2-(4-butoxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-12,12-difluoro-2-hydroxy-2-(2-methoxy-ethyl)-nonadec-4-enoic acid (No. 5514403, 100 mg, 0.142 mmol) was dissolved in acetonitrile (1.0 mL), and subsequently water (0.005 mL, 0.278 mmol), triethylamine (0.118 mL, 0.847 mmol) and anhydrous lithium bromide (244 mg, 2.81 mmol) were sequentially added at room temperature. The mixture was stirred at 50° C. for 11.5 hours. After cooling the reaction solution to room temperature, a preparative HPLC was performed to obtain 51.1 mg of the title compound (0.07629 mmol, 54% yield).

Provenance & Evidence