Acetone → HCID 59883971, compound

Participants

Reaction Steps

(S)-tyrosine methyl ester hydrochloride (23 g, 100 mmol) was added to an ethanolic solution of MeNH2 (60 mL, 8 M), and the resulting mixture was stirred at room temperature for 24 h. The excess MeNH2 was removed by distillation or by washing with THF several times until the N-methyl 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 2 was obtained as a white solid in 82% overall yield (19.2 g, 82 mmol) after silica gel chromatography (1:1 of EtOAc:Hex). 1H NMR (CDCl3): δ 7.09 (d, 2H), 6.74 (d, 2H), 3.82 (t, 1H), 3.06 (m, 2H), 2.78 (s, 3H), 1.32 (s, 3H), 1.22 (s, 3H). Elemental analysis for C13H18N2O2 (2)—calculated: C 66.64, H 7.74, N 11.96%; observed: C 66.24, H 7.70, N 12.10%.

Provenance & Evidence