Citric Acid → HCID 90060310, compound

Participants

Reaction Conditions

Reaction Steps

tert-Butyl (E)-(2S,3S)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-[(S)-1-ethoxycarbonyl-2-(4-hydroxy-phenyl)-ethylcarbamoyl]-11-(2-heptyl-[1,3]dioxolan-2-yl)-2-hydroxy-undec-4-enoate (909 mg) was dissolved in acetonitrile (9.0 mL), and an aqueous solution (3.6 mL) of 0.5 M citric acid was added. The mixture was stirred at 60° C. for 3 hours. Water was then added to the reaction mixture, which was followed by extraction with a mixed solvent of ethyl acetate/n-hexane. The organic extract was dried over magnesium sulfate, and concentrated under reduced pressure to obtain a crude product (660 mg). The obtained crude product (182 mg) was dissolved in DMF, and potassium carbonate (49.4 mg) and 1-bromo-but-2-yne (28.9 μL) were added. The mixture was stirred at room temperature for 20 hours. Water was then added to the reaction mixture, which was followed by extraction with a mixed solvent of ethyl acetate/n-hexane. The organic layer was washed with a saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound (74 mg).

Provenance & Evidence