Triethylamine → HCID 58980322, compound

Participants

Reaction Steps

To a stirred solution at room temperature of 4-acetylbenzoic acid (395 mg, 2.41 mmol) in anhydrous DMF (15 ml) under nitrogen were added Et3N (369 μl, 2.65 mmol) and BOP reagent (1.171 g, 2.65 mmol), respectively. After 30 min, a solution of t-butyl (2-amino-phenyl)-carbamate (551 mg, 2.65 mmol), Et3N (1.01 ml, 7.22 mmol) in anhydrous DMF (5 ml) was added dropwise. After 19 h, the reaction mixture was poured into a saturated aqueous solution of NH4Cl, and diluted with AcOEt. After separation, the organic layer was successively washed with sat NH4Cl, H2O and brine, dried over anhydrous MgSO4, filtered and concentrated. The crude residue was then purified by flash chromatography on silica gel (AcOEt/hexane:40/60→50/50) to afford the title compound III (500 mg, 1.41 mmol, 59% yield) as a yellow solid. 1H NMR (300 MHz, CDCl3) δ(ppm): 9.47 (bs, 1H), 8.10–8.00 (m, 4H), 7.91 (d, J=7.9 Hz, 1H), 7.33–7.15 (m, 3H), 6.67 (s, 1H), 2.67 (s, 3H), 1.53 (s, 9H).

Provenance & Evidence