1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-(4-fluoro-3-methoxyphenyl)-N-methoxy-N,2-dimethylpropanamide

Participants

Reaction Steps

To a solution of 2-(4-fluoro-3-methoxyphenyl)-2-methylpropanoic acid (114.75 g, 4.71 mmol) in DCM (2 L) was added N,O-dimethylhydroxylamine hydrochloride (79 g, 0.81 mol), EDCI (145 g, 0.72 mol), DMAP (33 g, 0.27 mol), and DIPEA (471 mL, 2.7 mol). The resulting mixture was stirred 5 h and quenched with H2O (1 L). The organic layer was washed with 1N HCl (1 L×2), satd NaHCO3 (1 L), and brine (1 L) successfully. The organic phase was dried over MgSO4 and concentrated at reduced pressure to afford 2-(4-fluoro-3-methoxyphenyl)-N-methoxy-N,2-dimethylpropanamide as yellow color oil (123 g, 89%). 1H NMR (400 MHz, CDCl3): δ 7.03 (t, 1H), 6.83 (d, 1H), 6.80 (m, 1H), 3.89 (s, 3H), 3.12 (s, 3H), 2.77 (s, 3H), 1.53 (s, 6H).

Provenance & Evidence