Pyridine → Benzyl 2-(3-fluoro-4-(2-hydroxy-3-(methoxycarbonyl)phenylcarbamyl)phenyl)pyrrolidine-1-carboxylate

Participants

Reaction Steps

To a stirred solution of methyl 3-amino-2-hydroxybenzoate (3.4 g, 20.4 mmol) and pyridine in anhydrous dichloromethane (35 mL) was added dropwise a solution of benzyl 2-(4-(chlorocarbonyl)-3-fluorophenyl)pyrrolidine-1-carboxylate (8.87 g, 24.5 mmol) in anhydrous dichloromethane (90 mL). After the addition, the mixture was stirred at room temperature overnight. The mixture was diluted with dichloromethane, washed with water, 1N HCl, brine, dried over anhydrous sodium sulfate, and concentrated, re-crystallized from ethyl acetate to give benzyl 2-(3-fluoro-4-(2-hydroxy-3-(methoxycarbonyl)phenylcarbamyl)phenyl)pyrrolidine-1-carboxylate as white solid (8.20 g, yield 68%). 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 1.77-1.87 (m, 3H), 2.33-2.37 (m, 1H), 3.55-3.58 (m, 1H), 3.64-3.70 (m, 1H), 3.83 (s, 3H), 4.86-5.07 (m, 3H), 6.65 (s, 1H), 6.92 (s, 1H), 7.19-7.39 (m, 6H), 7.48-7.51 (m, 1H), 7.82-7.84 (m, 1H), 8.25-8.30 (m, 1H), 9.86 (br s, 1H), 10.99 (br s, 1H); LC-MS (ESI) m/z: 493 (M+1)+.

Provenance & Evidence