Lithium Hydroxide → (S)-3-(4-(3,4-Bis(trifluoromethoxy)benzyloxy)phenyl)-3-(isoxazol-3-yl)propanoic acid

Cesium carbonate (137 mg, 0.4 mmol) was added to a mixture of 4-(bromomethyl)-1,2-bis(trifluoromethoxy)benzene 22.1 (71 mg, 0.21 mmol) and 7.5 (82 mg, 0.21 mmol) in DMF (2 mL). The mixture was stirred at room temperature for 16 hours. To the reaction mixture was added LiOH in water (0.5 mL, 1N solution) and THF (1 mL). The mixture was stirred at 23° C. for 3 hours. The mixture was filtered and purified by reverse phase HPLC to give 22 (19 mg) after lyophilization. MS ESI (pos.) m/e 492.1 (M+H). 1H NMR (400 MHz, CDCl3) δ 8.31 (1H, s), 7.45 (1H, s), 7.39 (2H, s), 7.21 (2H, d, J=8.3 Hz), 6.93 (2H, d, J=8.8 Hz), 6.08 (1H, s), 5.05 (2H, s), 4.57 (1H, t, J=7.6 Hz), 3.37 (1H, dd, J=16.6, 7.8 Hz), 3.00 (1H, dd, J=16.6, 7.8 Hz).

1. stirringThe mixture was stirred at 23° C. for 3 hours
2. filtrationThe mixture was filtered
3. custompurified by reverse phase HPLC

ORD record

ord-48dd3a8948d44d5d8fbd5b53ce384cbb

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07714008B2