Acetic Anhydride → HCID 90060443, compound

Participants

Reaction Steps

tert-Butyl (E)-(2S,3S)-2-hydroxy-2-(2-hydroxy-ethyl)-3-[(S)-2-(4-hydroxy-phenyl)-1-(5-methyl-oxazol-2-yl)-ethylcarbamoyl]-12-oxo-nonadec-4-enoate (3.5 mg, 5.22 μmol) was dissolved in DMF (0.3 mL), and potassium carbonate (1.4 mg, 10.4 μmol) and 1-bromo-but-2-yne (0.7 μL, 7.83 μmol) were added. The mixture was stirred at room temperature for 24 hours. A saturated brine was then added to the reaction mixture, which was followed by extraction with ethyl acetate. The organic extract was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was dissolved in dichloromethane (0.5 mL), and acetic anhydride (1.0 μL, 10.4 μmol), DMAP (0.06 mg, 0.52 μmol), and triethylamine (2.9 μL, 20.9 μmol) were added. The mixture was stirred at room temperature for 9 hours. A saturated brine was then added to the reaction mixture, which was followed by extraction with ethyl acetate. The organic extract was dried over magnesium sulfate, and concentrated under reduced pressure to obtain the title compound (4 mg).

Provenance & Evidence