Bis-(1H-imidazol-2-YL)-methanone → HCID 90337941, compound

Participants

Reaction Steps

To a solution of (R)-ethyl 4-(5′-fluoro-2′-methoxy-[1,1′-biphenyl]-4-yl)-3-(2-hydrazinyl-2-oxoacetamido)butanoate (4.7 g, 11 mmol) in THF (115 mL) was added carbonyl diimidazole (2.4 g, 14 mmol) and the reaction mixture was stirred at room temperature for 24 hours then concentrated to a yellow oil than was purified by silica gel chromatography (40-45% ethyl acetate/hexane) to afford (R)-ethyl 4-(5′-fluoro-2′-methoxy-[1,1′-biphenyl]-4-yl)-3-(5-oxo-4,5-dihydro-1,3,4-oxadiazole-2-carboxamido)butanoate 4.25 g (84%). LCMS Method 1 retention time 1.57 min ES+ M+H(+) 443.8; LCUV Method 2 retention time 7.44 min; 1H NMR (400 MHz, MeOH-d) δ ppm 7.44 (d, J=8.0 Hz, 2H), 7.29 (d, J=8.0 Hz, 2H), 7.03-7.05 (m, 3H), 4.67 (t, 1H), 4.12 (q, J=7.2 Hz, 2H), 3.76 (s, 3H), 2.96 (d, J=6.8 Hz, 2H), 2.66 (d, J=6.8 Hz, 2H), 1.24 (t, J=7.2 Hz, 3H)

Provenance & Evidence