N,N-Diethylethanamine trihydrofluoride → HCID 57978313, compound

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Reaction Steps

A mixture of 3-[2-({(2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)-2-methylpropyl]-N-[2-(2-chlorophenyl)ethyl]benzamide (preparation 118), (147 mg, 0.24 mmol) and triethylamine trihydrofluoride (39 μL, 0.24 mmol) was stirred at room temperature for 3 days. The mixture was then concentrated in vacuo and the residue was purified by column chromatography on silica gel, eluting with dichloromethane:methanol:0.88 ammonia, 100:0:0 to 95:5:0.5. The appropriate fractions were evaporated under reduced pressure and the residue was azeotroped with methanolic ammonia to afford the title compound as a colourless solid in 77% yield, 75 mg. 1H NMR (400 MHz, CD3OD) δ: 7.61 (2H, m), 7.37-7.29 (5H, m), 7.23-7.16 (2H, m), 7.12 (1H, dd), 6.74 (1H, d), 4.66 (1H, m), 4.64 (2H, s), 3.63 (2H, m), 3.05 (2H, t), 2.96-2.84 (2H, t), 2.76-2.69 (2H, m), 1.10 (3H, s), 1.04 (3H, s) ppm; LRMS ESI m/z 497 [M+H]+.

Provenance & Evidence