Reaction #9942

Reaction equation

3-(3-ethoxy-4-methoxyphenyl)-3-(4-nitrophthalimido)propanoic acid

carbonyldiimidazole

O-benzylhydroxylamine hydrochloride

→

N-benzyloxy-3-(3-ethoxy-4-methoxyphenyl)-3-(4-nitrophthalimido)-propionamide

Yield 59.0%

Solvents

tetrahydrofuran

Conditions

Procedure

N-Benzyloxy-3-(3-ethoxy-4-methoxyphenyl)-3-(4-nitrophthalimido)propionamide was prepared by the procedure of Example 1 from 3-(3-ethoxy-4-methoxyphenyl)-3-(4-nitrophthalimido)propanoic acid (2.84 g, 6.85 mmol), carbonyldiimidazole (1.22 g, 7.52 mmol) and O-benzylhydroxylamine hydrochloride (1.32 g, 8.27 mmol) in tetrahydrofuran (15 mL) to afford N-benzyloxy-3-(3-ethoxy-4-methoxyphenyl)-3-(4-nitrophthalimido)-propionamide as a yellow solid (2.1 g, 59% yield): mp, 159.0–161.0° C.; 1H NMR (DMSO-d6) δ 1.30 (t, J=6.9 Hz, 3H, CH3), 3.03 (dd, J=7.7, 14.8 Hz, 1H, CHH), 3.15 (dd, J=8.0, 14.9 Hz, 1H, CHH), 3.72 (s, 3H, CH3), 3.96 (q, J=6.9 Hz, 2H, CH2), 4.64 (s, 2H, PhCH2), 5.66 (t, J=7.8 Hz, 1H, NCH), 6.87–6.95 (m, 2H, Ar), 6.99 (br s, 1H, Ar), 7.23–7.41 (m, 5H, Ar), 8.06 (t, J=7.7 Hz, 1H, Ar), 8.14–8.18 (m, 1H, Ar), 8.26–8.31 (m, 1H, Ar), 11.24 (br s, 1H, NH); 13C NMR (DMSO-d6) δ 14.66, 34.09, 50.62, 55.46, 63.72, 76.69, 111.86, 112.46, 119.83, 122.47, 126.94, 128.18, 128.67, 130.28, 133.08, 135.79, 136.38, 144.36, 147.69, 148.68, 162.99, 165.69, 166.18. Anal. Calcd for C27H25N3O8: C, 62.42; H, 4.85; N, 8.09. Found: C, 62.12; H, 4.92; N, 7.82.

Source