Lithium Hydroxide → HCID 3836387, compound

Participants

Reaction Steps

A solution of ethyl 2-(3-benzylureido)-3-phenylpropanoate 13 (2.66 mmol, 0.83 g) and 2 N lithium hydroxide (5.32 mmol, 0.22 g) in ethanol (20 mL) was kept in stirring overnight at room temperature. The reaction was quenched by addition of 2 N HCl until pH=2, afterwards the precipitate was filtered, washed with water (3×30 mL) and dried to obtain the pure 2-(3-benzylureido)-3-phenylpropanoic acid as a pale white solid; 95% yield, m.p. 115-117° C.; recryst. solvent: cyclohexane/benzene; 1H NMR (CDCl3, 400 MHz, δ; ppm) δ 2.85-2.87 (dd, 1H, PhCHHCHCOO), 2.89-2.91 (dd, 1H, PhCHHCOO), 4.38-4.40 (m, 1H, PhCHHCHCOO), 6.14-6.17 (d, 1H, PhCHHNHCONH), 6.54-6.57 (m, 1H, PhCHHNHCONH), 7.18-7.30 (m, 10H, aromatic protons), 12.65 (bs, 1H, COOH); 13C NMR (CDCl3, 400 MHz, δ; ppm) δ 36.0, 44.4, 56.8, 125.9, 126.7, 126.9 (2C), 127.7 (2C), 128.5 (2C), 128.6 (2C), 136.6, 137.9, 157.6, 174.7; MS (ESI) m/z: 298.32 [M]+.

Provenance & Evidence