Methyl iodide → HCID 86587806, compound

Participants

Reaction Steps

To a stirred solution of methyl (S)-4-[2-(trifluoroacetamido)-1-propoxy]benzoate (695 mg, 2.28 mmol) and K2CO3 (630 mg, 4.56 mmol) in DMF (10 ml) was added MeI (210 ml, 3.37 mmol) and the reaction mixture was stirred at room temperature for 2 days. The mixture was diluted with H2O and extracted with EtOAc. The extract was washed with brine, dried over Na2SO4, and evaporated. The residue was purified by column chromatography on silica-gel with EtOAc-CHCl3 (1:19, v/v) as eluent to give methyl (S)-4-[2-[(N-methyl)trifluoroacetamido]-1-propoxy]benzoate (720 mg, 99%) as a white solid. mp 73–75° C.; 1H-NMR (CDCl3) δ 1.36–1.39 (m, 3 H), 2.96 and 3.10 (each s, total 3 H), 3.89 (s, 3 H), 3.99–4.14 (m, 2 H), 4.84–4.92 (m, 1 H), 6.88–6.92 (m, 2 H), 7398–8.00 (m, 2 H); MS (FAB) m/z 320 (M++1); Anal. Calcd for C14H16F3NO4: C, 52.67; H, 5.05; F, 17.85; N, 4.39. Found: C, 52.76; H, 5.09; F, 17.53; N, 4.32.

Provenance & Evidence