Beta-Alanine → Epimerox

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2-(5-oxo-2-thioxoimidazolidin-1-yl)-3-phenylpropanoic acid (0.110g, 0.416 mmol) and 5-(3,4-dichloro-phenyl)thiophene-2-carbaldehyde (0.100 g, 0.416 mmol) in acetic acid 10 mL is added β-alanine (1.8 mg, 0.021 mmol) and heat to 80° C. for 16 h. The resulting reaction mixture is cooled down and the solvent is removed. The pure product (0.070 g, 0.144 mmol, red solid) is obtained by column chromatography using MeOH/DCM, 2-7% ration solvent system. The product is further purified by recryatallization in hexane and DCM mixture and got pure E-isomer. 1H-NMR (CDCl3/CD3OD/300 MHz): 7.84 (d, J=2.1 Hz, 1H), 7.60 (dd, J=8.7, 2.4 Hz, 1H), 7.44 (d, J=2.7 Hz, 1H), 7.17 (m, 6H), 6.85 (m, 1H), 6.42 (s, 1H), 5.61 (dd, J=11.1, 5.4 Hz, 1H), 3.66 (dd, J=14.1, 12.6 Hz, 1H), 3.53 (dd, J=14.1, 5.1 Hz, 1H). MS (ES−, m/z): 585.3 (M−, 100.0).

Provenance & Evidence