Isobutyric Acid → HCID 73505387, compound

Participants

Reaction Steps

To a stirred solution of 5′-(3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl)-3′H-spiro[azetidine-3,1′-isobenzofuran]hydrochloride (Preparation 5, 900 mg, 1.76 mmol) in THF (20 mL) was added DIPEA (3.07 mL, 17.65 mmol), isobutyric acid (0.321 mL, 3.53 mmol) and T3P (5.12 mL, 8.82 mmol, 50% solution in ethyl acetate) at room temperature. The resulting reaction mixture was stirred at room temperature for 16 hours. Reaction was monitored by TLC, after complete consumption of staring material reaction mixture was quenched with water (30 mL) and extracted with ethyl acetate (3×25 mL). Combined organic layer was washed with NaHCO3 solution (30 mL), brine (30 mL), dried over sodium sulphate and concentrated to get sticky solid (1 g, crude). The crude was purified by column chromatography using 100-200 mesh silica gel. Desired compound was eluted in 0.5% MeOH in DCM to get desired compound as pale green solid (0.4 g, 41.5%). 1H NMR (400 MHz, DMSO-d6) δ: 1.01-1.05 (m, 6H), 2.54-2.75 (m, 1H), 3.74 (d, J=17.8 Hz, 1H), 3.87 (d, J=17.92 Hz, 1H), 4.12 (s, 2H), 4.41-4.46 (m, 3H), 4.82 (d, J=17.36 Hz, 1H), 5.12 (s, 2H), 7.66 (d, J=7.96 Hz, 1H), 7.80 (s, 2H), 7.85 (s, 1H), 7.94 (d, J=7.92 Hz, 1H), LC-MS (m/z): 545.0 (M+H).

Provenance & Evidence