Water → HCID 11676374, compound

Participants

Reaction Steps

To a solution of methyl 4-({2-[[4-cyano-3-(trifluoromethyl)phenyl](2,2,2-trifluoroethyl)amino]ethyl}oxy)benzoate (0.0863 g, 0.193 mmol, Example 32) in THF (3 mL) at rt was added LiOH.H2O (0.041 g, 0.97 mmol) and water (0.30 mL). The mixture was stirred 19 h at rt, then 8 h at reflux, cooled and partitioned between 1 N NaOH/Et2O. Layers were separated, and the aqueous layer extracted with Et2O (×1). The aqueous layer was then acidified to approximately pH 1 by addition of 2N HCl and extracted with EtOAc (×3). Combined EtOAc extracts were washed with brine, dried over Na2SO4 and concentrated in vacuo yielding 0.0816 g of the title compound as a colorless film which crystallized when triturated with CDCl3: 1H NMR (400 MHz, CD3OD) δ 7.97-7.90 (m, 2H), 7.75 (d, J=8.9 Hz, 1H), 7.38 (d, J=2.3 Hz, 1H), 7.28 (dd, J=8.9, 2.5 Hz, 1H), 6.97-6.92 (m, 2H), 4.45 (q, J=8.8 Hz, 2H), 4.31 (t, J=5.2 Hz, 2H), 4.08 (t, J=5.2 Hz, 2H); MS (ESI) m/z 431 (M−1).

Provenance & Evidence