Sodium Hydroxide → HCID 44815647, compound

Participants

Reaction Steps

To a solution of (R)-{5-[3-chloro-4-(4-chloro-phenoxy)benzenesulfonylamino]-5,6,7,8-tetrahydro-naphthalen-1-yloxy}-acetic acid tert-butyl ester (160 mg, 0.277 mmol) in tetrahydrofuran (3 mL) was added 1N sodium hydroxide (3 mL). The reaction mixture was stirred at room temperature for 2 hours, and then extracted with diethyl ether (10 mL). The organic layer was discarded. The aqueous layer was acidified with concentrated hydrochloric acid to pH 4 and stirred with diethyl ether (3 mL) and petroleum ether (9 mL) at room temperature for 2 hours. The precipitate was collected by filtering through a glass funnel to afford (R)-{5-[3-chloro-4-(4-chloro-phenoxy)-benzenesulfonylamino]-5,6,7,8-tetrahydro-naphthalen-1-yloxy}-acetic acid (114 mg, 79%) as a white powder. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.21 (d, J=8.59 Hz, 1H), 8.02 (d, J=2.27 Hz, 1H), 7.82 (dd, J=8.59, 2.27 Hz, 1H), 7.53 (d, J=8.84 Hz, 2H), 7.13-7.23 (m, 2H), 7.05 (t, J=8.08 Hz, 1H), 6.67 (dd, J=11.75, 7.96 Hz, 2H), 4.65 (s, 2H), 4.39 (d, J=8.08 Hz, 1H), 1.78 (m, 2H), 1.59 (m, 4H); MS cald. For C24H21Cl2NO6S 521, obsd. 522 (ESI+) [(M+H)+].

Provenance & Evidence