Water → HCID 66652808, compound

Participants

Reaction Steps

To a stirred solution of tert-butyl 2-amino-3-methylbutanoate (Bachem, 6.3 g, 0.036 mol) in dry DMF (50 mL) under nitrogen, was added 4-cyano-2-fluoro-benzyl bromide (6.2 g, 0.029 mol) and NaHCO3 (6.09 g, 0.073 mol). The resulting mixture was stirred for 16 h at RT. Water (70 mL) was added and extracted with ethyl acetate (2×100 mL). The organic layer was washed with water (3×100 mL) and the solvent was dried over Na2SO4 and concentrated under vacuum. The resulted residue was purified by column chromatography using petroleum ether/ethyl acetate as eluent, affording the title compound as colorless liquid. 1H NMR (DMSO-d6, 400 MHz) δ 7.78 (d, J=10.2 Hz, 1H), 7.67 (t, J=1.5 Hz, 2H) 3.81 (m, 2H), 2.71 (m, 1H), 2.49 (m 1H), 1.81 (m, 1H), 1.37 (s, 9H), 0.88-0.84 (m, 6H).

Provenance & Evidence