Citric Acid → HCID 90060123, compound

Participants

Reaction Conditions

Reaction Steps

At room temperature, (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-12,12-difluoro-2-hydroxy-2-propyl-nonadec-4-enoic acid (No. 5501824; 27.5 mg, 0.041 mmol) was dissolved in acetonitrile (0.55 mL) and water (22 μL), and triethylamine (34.6 μL, 0.249 mmol) and lithium bromide (72.0 mg, 0.829 mmol) were added in order. The mixture was stirred at 50° C. for 2.0 hours, and cooled to room temperature. The progress of the reaction was then stopped by adding an aqueous solution of 0.5 M citric acid. Ethyl acetate was added, and the mixture was extracted. The organic layer was washed with water, dried over anhydrous sodium sulfate, and filtered. The solvent was distilled off. The residue was then purified by preparative HPLC (water with 0.05% TFA-acetonitrile with 0.05% TFA) to obtain (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-carboxy-ethylcarbamoyl]-12,12-difluoro-2-hydroxy-2-propyl-nonadec-4-enoic acid (No. 5501825; 22.4 mg, 84% yield, white powder).

Provenance & Evidence