4-Methylmorpholine → Methyl 4-{[3-(1,3-benzodioxol-5-yl)propanoyl]amino}benzoate

Participants

Reaction Steps

To a solution of 3-(3,4-methylenedioxyphenyl)-propionic acid (501 mg, 2.58 mmol) in anhydrous THF (10 mL) were added N-methylmorpholine (0.28 mL, 2.58 mmol) and isobutylchloroformate (0.33 mL, 2.58 mmol) at 0° C. After 30 min, at 0° C., a solution of methyl 4-aminobenzoate (390 mg, 2.58 mmol) in anhydrous THF (2 mL) was added to the reaction mixture. After 30 min the temperature was allowed to warm up to rt and stir for 24 hrs. After extraction with EtOAc (100 mL), washing with HCl (0.1N, 50 mL) and a saturated aqueous solution of NaHCO3 (50 mL), the organic layer was dryed over sodium sulfate and evaporated under vacuo to give a solid. The residue was taken up in Et2O, filtrated and washed with Et2O gave the title compound as a white solid (62%) in 99.4% purity by HPLC (MaxPlot detection between 230 and 400 nm).

Provenance & Evidence