Trifluoroacetic acid → HCID 86668784, compound

Participants

Reaction Steps

Trifluoroacetic acid (50 mL, 650 mmol) was added to a solution of (+/−)-ethyl 4-{4-[(tert-butoxycarbonyl)amino]phenyl}-2-methyl-2-(methylsulfonyl)butanoate (6.47 g, 16.2 mmol) in dicholoromethane (100 mL) at 0° C. The reaction was allowed to warm to room temperature and was stirred for 2 hours. The reaction was then concentrated; the residue was dissolved in 1N aqueous HCl (100 mL) and washed with ethyl acetate (3×100 mL). The organic layers were discarded. The aqueous layer was made basic with 1N aqueous NaOH, and extracted with ethyl acetate (3×100 mL). The combined organics were washed with water (100 mL), brine (100 mL), dried (MgSO4), filtered, and concentrated in vacuo to afford a crude orange oil. The crude product was purified via flash chromatography using an Analogix SF40-150 g column and an eluant of ethyl acetate in heptane (1:1) to afford the title compound as a yellow oil (3.52 g, 72.6%). LC-MS m/z 300.5 (M+1). 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.55 (t, J=7.13 Hz, 3H) 1.88 (s, 3H) 2.24-2.39 (m, 1H) 2.56-2.77 (m, 2H) 2.84-2.98 (m, 1H) 3.31 (s, 3H) 4.42-4.49 (m, 2H) 6.91 (d, J=8.40 Hz, 2H) 7.19 (d, J=8.40 Hz, 2H).

Provenance & Evidence