2-Phenylpropionic acid → HCID 18334080, compound

Participants

Reaction Steps

Oxalyl chloride (0.8 ml) and N,N-dimethylformamide (1 drop) were added to a solution of 2-phenylpropionic acid (900 mg) in methylene chloride (10 ml). This mixture was stirred at ambient temperature for 2 hours. The reaction mixture was then concentrated by evaporation under reduced pressure to afford a yellow oil. A solution of 3-methoxy-4-[3-(4-methoxyphenylamino)phenyl]amino-3-cyclobutene-1,2-dione (576 mg) [prepared as described in step (a) above] in N,N-dimethylacetamide (4 ml) was added to a solution of the oil in N,N-dimethylacetamide (4 ml) in an ice bath. The mixture was stirred at ambient temperature for 3 hours. At the end of this time, the reaction mixture was partitioned between a saturated aqueous solution of sodium hydrogencarbonate and ethyl acetate. The ethyl acetate layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated by evaporation under reduced pressure. The residue was purified by chromatography through a silica gel column using a 2:1 by volume mixture of methylene chloride and ethyl acetate as the eluant, to afford the title compound (603 mg) as a purple foamy solid.

Provenance & Evidence