Sodium hydride → HCID 10289584, compound

Participants

Reaction Steps

4-Chlorobenzyl bromide (0.037 g, 0.179 mmol) and tetrabutyl ammonium iodide (catalytic amount) are added to a 0° C. suspension of 2-(2-Fluoro-phenoxy)-2-methyl-3-{4-[2-(3-methyl-2-oxo-imidazolidin-4-yl)-ethoxy]-phenyl}-propionic acid ethyl ester (0.053 g, 0.119 mmol) and sodium hydride (0.012 g, 0.298 mmol, 60% suspension on mineral oil), pre-stirred for 1 h at ambient temperature. The reaction mixture is stirred at ambient temperature for 18 h, diluted with ethyl acetate, and washed. The organic layer is dried, concentrated, and purified by LCMS to provide the title compound. 1H NMR (400 MHz, CDCl3): δ 7.31-7.21 (m, 4H), 7.16 (d, 2H, J=8.3 Hz), 7.11-7.00 (m, 4H), 6.74 (d, 2H, J=8.3 Hz), 4.33, 4.31 (ABq, 2H, J=15.5 Hz), 3.96 (t, 2H, J=6.0 Hz), 3.71-3.64 (m, 1H), 3.39 (t, 1H, J=8.3 Hz), 3.29, 3.17 (ABq, 2H, J=14.3 Hz), 3.01 (t, 1H, J=8.3 Hz), 2.84 (s, 3H), 2.25-2.20 (m, 1H), 1.93-1.84 (m, 1H), 1.41 (s, 3H). MS [ES+] m/z exact mass calcd for C29H31N2O5 541.1906, found 541.1913.

Provenance & Evidence