1,1'-Carbonyldiimidazole → (3R)-3-(3-ethoxy-4-methoxyphenyl)-N-hydroxy-3-phthalimidopropionamide

Participants

Reaction Steps

(3R)-3-(3-Ethoxy-4-methoxyphenyl)-N-hydroxy-3-phthalimidopropionamide was prepared by the procedure of Example 1 from (3R)-3-(3-ethoxy-4-methoxyphenyl)-3-phthalimidopropanoic acid (14.6 g, 39.5 mmol), carbonyldiimidazole (7.1 g, 43.5 mmol) and hydroxylamine hydrochloride (3.3 g, 47.4 mmol) in tetrahydrofuran (50 mL) to afford (3R)-3-(3-ethoxy-4-methoxyphenyl)-N-hydroxy-3-phthalimidopropionamide as a white solid (13.9 g, 91% yield): mp, 257.0–259.5° C.; 1H NMR (DMSO-d6) δ 1.31 (t, J=6.9 Hz, 3H, CH3), 3.11 (d, J=7.9 Hz, 2H, CH2), 3.72 (s, 3H, CH3), 3.97 (q, J=6.9 Hz, 2H, CH2), 5.67 (t, J=7.8 Hz, 1H, NCH), 6.90 (br s, 2H, Ar), 7.02 (br s, 1H, Ar), 7.86 (br s, 4H, Ar), 8.79 (br s, 1H, OH), 10.59 (br s, 1H, NH); 13C NMR (DMSO-d6) δ 14.67, 34.22, 50.18, 55.44, 63.71, 111.73, 112.36, 119.65, 123.11, 131.18, 131.21, 134.56, 147.67, 148.53, 165.97, 167.61. Anal Calcd for C20H20N2O6: C, 62.49; H, 5.24; N, 7.29. Found: C, 62.79; H, 5.24; N, 7.23;

Provenance & Evidence