Hydrochloric Acid → HCID 68514769, compound

Participants

Reaction Steps

To a mixture of N-{(2S)-2-[N-(3-Chloropropyl)-N-methylamino]-2-methoxy-carbonylethyl}-N-[4-(4-trifluoromethylphenoxy)phenyl]methanesulfonamide (350 mg, 0.67 mmol) from Step D in THF (1.5 mL) was added lithium hydroxyl (1.0 M in H2O, 1.34 mL, 1.34 mmol) at room temperature. The mixture was stirred at rt for 3 h. Then, HCl(aq) (2 N, 0.67 mL, 0.67 mmol) and hexane (15 mL) were added sequentially. The resulting solid was filtered and was washed with H2O (50 mL) and hexane (100 mL). The solid was then dried to give 317 mg of the titled compound (92%) as a pale brown solid. 1H NMR (300 MHz, d6-DMSO) δ 12.60 (br s, 1H), 7.76 (d, J=9.0 Hz, 2H), 7.46 (d, J=9.0 Hz, 2H), 7.19 (d, J=9.0 Hz, 2H), 7.16 (d, J=9.0 Hz, 2H), 3.96-3.80 (m, 2H), 3.59 (t, J=9.0 Hz, 2H), 3.20 (t, J=7.5 Hz, 1H), 3.00 (s, 3H), 2.67-2.46 (m, 2H), 2.20 (s, 3H), 1.82-1.70 (m, 2H); MS (EI) 509 (M++1), 507 (M+−1, 100).

Provenance & Evidence