Sodium hydride → HCID 59003218, compound

Participants

Reaction Steps

Add a solution of 2-isopropoxycarbonylamino-6-methyl-benzoic acid methyl ester (3.77 g, 15.0 mmol) in DMF (60 mL) to a suspension of sodium hydride 60% dispersion mineral oil (600 mg, 15.0 mmol) in DMF (60 mL) at 0° C. under an atmosphere of nitrogen and allow to reach room temperature over 1 h. Add ethyl 4-bromobutyrate (3.2 mL, 22 mmol) and stir at room temperature for 14 h. Dilute with ethyl acetate, wash with 1M HCl, water and brine. Dry the organic layer over anhydrous sodium sulfate, filter and remove the solvent under reduced pressure. Purify the residue by flash chromatography, eluting with hexanes/ethyl acetate, to provide the title compound (4.60 mg, 84%): 1H NMR (CDCl3, 300 MHz) δ 1.05-1.30 (m, 9H), 1.90 (m, 2H), 2.32 (m, 2H), 2.36 (s, 3H), 3.85 (s, 3H), 4.11 (q, J=7.3 Hz, 2H), 4.88 (m, 1H), 7.02 (m, 1H), 7.16 (d, J=7.7 Hz, 1H), 7.31 (t, J=7.9 Hz, 1H). MS (ES+): 366 (M+H).

Provenance & Evidence