Malonic Acid → 3-Amino-3-(3-cyclopentyloxy-4-methoxyphenyl)propanoic acid

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of 3-cyclopentyloxy-4-methoxybenzaldehyde (54.9 grams, 249 mmol) and ammonium acetate (58.2 grams, 748 mmol) in ethanol (200 mL, 95%) was heated to 45° C. To the yellowish suspension, was added malonic acid (25.9 grams, 249 mmol) as a solid. The mixture was refluxed for 16 h. The mixture was cooled to room temperature. The suspension was filtered and the solid was washed with cold ethanol (200 mL) until the color was removed. The white solid was dried in a vacuum oven (45° C., 1 torr) to afford 3-amino-3-(3'-cyclopentoxy-4'-methoxyphenyl)propionic acid as white solid (41.97 grams, 61% yield): mp, 234.0°-235.0° C.; 1H NMR (CDCl3)δ1.62-1.98 (m, 8H, C5H8), 2.53 (d, J=7 Hz, 2H, CH2), 3.80 (s, 3H, CH3), 4.21 (t, J=7 Hz, 1H, OCH), 4.84-4.86 (m, 1H, NCH), 6.96-7.03 (m, 3H, Ar); 13C NMR (CDCl3)δ26.33, 34.97, 49.78, 55.32, 58.48, 83.99, 114.99, 116.04, 121.63, 140.63, 149.12, 150.75, 182.87; Anal Calcd for C15 H21NO4 : C, 64.50; H, 7.58; N, 5.01. Found: C, 64.54; H, 7.68; N, 4.93.

Provenance & Evidence