Acetone → HCID 53483228, compound

Participants

Reaction Steps

(S)-phenylalanine methyl ester hydrochloride (21.5 g, 100 mmol) was added to ethanolamine (48 mL, 800 mmol), and the resulting mixture was stirred at room temperature for 24 h. The excess ethanolamine was removed by distillation until the N-(2-hydroxylethyl) amide product was obtained as a white solid. Dry MeOH (200 mL) and dry acetone (40 mL) were added to this residue. The resulting solution was stirred at 60° C. for 24 h, cooled to room temperature, and then concentrated in vacuo. Compound 6 was obtained as a white solid in 55% overall yield (13.6 g, 55 mmol) after silica gel chromatography (2:1 of EtOAc:Hex). 1H NMR (CDCl3): δ 7.2-7.34 (m, 5H), 3.85 (t, 1H), 3.60-3.70 (m, 2H), 3.42 (m, 1H), 3.14 (m, 2H), 3.09 (d, 2H), 1.28 (s, 3H), 1.13 (s, 3H). Elemental analysis for C14H20N2O2 (6)—calculated: C 67.71, H 8.12, N 11.28%; observed: C 67.12, H 7.99, N 11.52%.

Provenance & Evidence