Cesium carbonate → (2R)-2-[N-(4-Allyloxy-3-fluorobenzyl)-N-(4-chlorobenzenesulfonyl)amino]-4-methyl-pentanoic acid amide

Participants

Reaction Steps

To a solution of (2R)-2-(4-chlorobenzenesulfonylamino)-4-methyl-pentanoic acid amide (1.00 g, 3.29 mmol), and Cs2CO3 (1.29 g, 3.95 mmol) in DMF (25 mL) was added 1-allyloxy-4-bromomethyl-2-fluorobenzene (ref.: Graham, Samuel L; et al., Eur. Pat. Appl. (1992): EP 487270; 0.88 g, 3.67 mmol). The resulting solution was stirred at rt for 18 h. The reaction was then diluted with 9:1 EtOAc:hexanes (350 mL) and washed with H2O (4×200 mL), brine, and dried over Na2SO4, to afford the titled compound (393 mg) as a white solid in 26% yield. MS (ESI), (M+H)+ 469.1; 1H NMR (CDCl3) δ 7.66 (d, 2H, J=8.1), 7.45 (d, 2H, J=8.1), 7.11 (d, 1H, J=12.0), 6.98 (m, 1H), 6.84 (t, 1H, J=8.0), 6.22 (br s, 1H), 6.04 (m, 2H), 5.42 (m, 1H), 5.16 (br s, 1H), 4.59 (m, 2H), 4.40 (m, 3H), 1.83 (m, 1H), 1.32 (m, 1H), 1.14 (m, 1H), 0.76 (d, 3H, J=7.0), 0.68 (d, 3H, J=7.0).

Provenance & Evidence