Malonic Acid → 3-amino-3-(3,4,5-trimethoxyphenyl)propanoic acid

Participants

Reaction Steps

3,4,5-Trimethoxy benzaldehyde (10 mmol, 1 eq), malonic acid (1 eq) and ammonium acetate (1.3 eq) are suspended in EtOH and refluxed for 16 h (Tetrahedron, 58 (2002) 7449-7461). Upon cooling to room temperature a white precipitate is formed. The mixture is concentrated in vacuo and the white solid is partitioned between EtOAc and dilute aqueous HCl (pH 2). The aqueous phase is concentrated in vacuo. 3-Amino-3-(3,4,5-trimethoxy-phenyl)propionic acid (crude product) is obtained as a white solid (51% yield); ES-MS (MH+)=239.0 (M-NH2).

Provenance & Evidence