3',4'-Dimethoxycinnamic acid → HCID 67343122, compound

Participants

Reaction Steps

1.0 mL of Methylene chloride, 0.010 mL of N,N-dimethylformamide and 0.064 mL of oxalyl chloride were added to 0.13 g of 3,4-dimethoxycinnamic acid at room temperature sequentially and stirred at the same temperature for 1 hour. The reaction mixture was added to a mixed solution of 1.5 mL of methylene chloride and 0.14 mL of triethylamine containing 0.15 g or tert-butyl 2-amino-4-phenethylbenzoate while ice-cooled and stirred at room temperature overnight. The solvent was evaporated under reduced pressure and ethyl acetate and 10% critic acid aqueous solution were added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed, with 10% citric acid aqueous solution, a saturated sodium hydrogen carbonate aqueous solution and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia chemical Ltd., eluent; hexane:ethyl acetate=4:1] to obtain 0.12 g of tert-butyl 2-((E)-3-(3,4-dimethoxyphenyl)acrylamido)-4-phenethylbenzoate as white solid.

Provenance & Evidence