Sodium Bicarbonate → HCID 66621319, compound

Participants

Reaction Steps

A mixture of benzyl 4-(2-hydroxy-3-(methoxycarbonyl)phenylcarbamoyl)piperidine-1-carboxylate (2.63 g, 6.4 mmol) in propionic acid (10 mL) was heated to reflux for 4 days. The mixture was diluted with water (50 mL), neutralized with sodium bicarbonate, and then extracted with ethyl acetate (50 mL×3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated to give crude product. The crude product was purified by prep-HPLC to afford methyl 2-(1-(benzyloxycarbonyl)piperidin-4-yl)benzo[d]oxazole-7-carboxylate (560 mg, yield 22%). 1H-NMR (400 MHz, CDCl3) δ (ppm): 1.94-1.98 (m, 2H), 2.20-2.23 (m, 2H), 3.07-3.09 (m, 2H), 3.21-3.24 (m, 1H), 4.00 (s, 3H), 4.23 (brs, 2H), 5.16 (s, 2H), 7.32-7.40 (m, 6H), 7.87-7.89 (dd, J1=7.6 Hz, J2=0.8 Hz, 1H), 7.95-7.97 (dd, J1=8.0 Hz, J2=0.8 Hz, 1H); LC-MS (ESI) m/z: 395 (M+1)+.

Provenance & Evidence