2-Benzoylcyclohexanone → 2-(2-Benzoyl-phenylamino)-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-naphthalen-1-yl}-propionic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

0.345 g of 2-Amino-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-naphthalen-1-yl}-propionic acid ethyl ester was dissolved in 6 ml of anisole and treated successively with 0.181 g (1.15 eq.) of 2-benzoyl-cyclohexanone and 60 mg of Pd/C (10%) and heated under Ar to 180-185° C. After 80 Min., additional 60 mg of fresh catalyst was added and heating continued for another 3.5 h. Cooling to RT, pouring onto crashed ice, twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and purification by flash chromatography (SiO2, hexane/AcOEt 7/3) produced 0.075 g of the title compound in the less polar fractions and 0.285 g of intermediate enamine, which was processed once again as just described. Final purification left a combined crop of 0.221 g of 2-(2-benzoyl-phenylamino)-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-naphthalen-1-yl}-propionic acid ethyl ester as yellow, sticky oil.

Provenance & Evidence