Trifluoroacetic acid → HCID 86622365, compound

Participants

Reaction Steps

Step BM (1). A solution of 3-amino-3-(3,5-dimethylphenyl)propanoic acid (18 g, 0.078 mol) and TFA (72 mL) was stirred at rt for 30 min. Trifluoroacetic anhydride (72 mL) was added and the resulting mixture was heated at reflux for 2 h. After cooling to rt, the reaction was concentrated in vacuo. The crude residue was dissolved in EtOAc and sequentially washed with 1 N NaOH and brine. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to afford 15 g (71% yield) of N-(4,6-dimethyl-3-oxo-2,3-dihydro-1H-inden-1-yl)-2,2,2-trifluoroacetamide as a white solid. LC-MS (M+H)+=272.09; 1H NMR (500 MHz, CDCl3) δ ppm 7.17 (s, 1H) 7.04 (s, 1H) 6.91 (d, J=6.71 Hz, 1H) 5.52-5.59 (m, 1H) 3.15 (dd, J=18.92, 7.93 Hz, 1H) 2.50 (s, 3H) 2.46 (d, J=3.36 Hz, 1H) 2.40 (s, 3H).

Provenance & Evidence