Acetamidomalonic acid diethyl ester → Ethyl 3-[2-(3-bromopropyl)phenyl]-2-acetamido-2-carboethoxypropanoate

Participants

Reaction Steps

To a stirred solution of 0.61 g (27 mmol) Na in 40 mL of dry ethanol was added portionwise 5.86 g (27 mmol) of solid diethyl acetamidomalonate. This mixture was stirred at reflux under nitrogen for 2 h, then cooled to 0°-10° C. on an ice bath. Then, 8.0 g (27 mmol) of 2-(3-bromopropyl)benzyl bromide in 40 mL of dry ethanol was rapidly added. The reaction mixture was stirred for 2 h at 0°-10° C., then 24 h at room temperature. The precipitated inorganic salt was removed by filtration, and was washed with 20 mL of ethanol and discarded. The combined solvents were removed under reduced pressure yielding an orange colored oil. This oil was chromatographed on a column of silica gel with hexane-ethyl acetate (3:1) as eluant. The combined fractions were concentrated under reduced pressure to yield an oil which solidified upon standing, yield 9.5 g (82%), mp 73°-74.5° C. IR(nujol): 1745, 1648 cm-1 (C=O). 1H NMR(D2O) δ 1.3 (t, 6H); 1.9-2.4 (m, 5H); 2.7 (t, 2H); 3.4 (t, 2H); 3.75 (5, 2); 4.3 (q, 4); 6.6 (s, 1H); 7.0-7.3 (m, 4H). Anal Calcd. for C19H26NO3Br: C, 53.28; H, 6.12; N, 3.27; Br, 18.66. Found: C, 53.33; H, 6.13; N, 3.23; Br, 18.67.

Provenance & Evidence