Acetic Anhydride → HCID 118260144, compound

Participants

Reaction Steps

A mixture of No. 4984967, tert-butyl (E)-(2S,3S)-3-[(S)-1-tert-butoxycarbonyl-2-(4-but-2-ynyloxy-phenyl)-ethylcarbamoyl]-2-hydroxy-2-(2-hydroxy-ethyl)-12-oxo-nonadec-4-enoate (112 mg, 0.152 mmol) and dichloromethane (1.3 mL) was cooled to 4° C., and acetic anhydride (35.8 μL, 0.379 mmol), triethylamine (23.3 μL, 0.167 mmol), and DMAP (1.9 mg, 0.02 mmol) were added. After stirring for 2 hours, the consumption of the starting materials was confirmed by LCMS. The solvent was distilled off under reduced pressure. Formic acid (10 mL) was added and the mixture was stirred at room temperature for 15 hours. Formic acid was distilled off under reduced pressure. The resulting residue was purified by preparative HPLC and then freeze-dried to obtain the title compound (46 mg, 45% yield, colorless oil).

Provenance & Evidence