Trifluoroacetic acid → Methyl 5-(azetidin-3-yl)-2-methyl-3-[methyl(oxan-4-yl)amino]benzoate

Participants

Reaction Steps

To a stirred solution of tert-butyl 3-[3-(methoxycarbonyl)-4-methyl-5-[methyl(oxan-4-yl)amino]phenyl]azetidine-1-carboxylate (400 mg, 0.96 mmol) in DCM (4 ml) was added TFA (1 ml) and the solution was stirred at room temperature for 45 min after which the solvent was evaporated to dryness and saturated aqueous NaHCO3 was added until pH7-8. The aqueous phase was extracted with DCM (3×30 ml), washed with brine (30 ml), dried with MgSO4, filtered and evaporated to afford the title compound as an orange oil (370 mg, 95%). LC-MS 96%, m/z=319.1, 1H NMR (500 MHz, Chloroform-d) δ 7.49 (d, J=1.4 Hz, 1H), 7.20 (d, J=1.3 Hz, 1H), 4.32-4.10 (m, 5H), 3.98 (d, J=11.0 Hz, 2H), 3.90 (d, J=8.4 Hz, 3H), 3.34 (t, J=10.8 Hz, 2H), 2.99 (ddd, J=14.7, 10.9, 3.8 Hz, 1H), 2.65 (d, J=8.3 Hz, 3H), 2.51-2.41 (m, 3H), 1.73 (ddd, J=15.7, 12.1, 4.3 Hz, 2H), 1.64 (d, J=11.2 Hz, 2H).

Provenance & Evidence