Ethanaminium, N,N,N-triethyl-, fluoride (1:1) → (3R)-3-((S)-1-(2-(2-ethylphenoxy)phenyl)-1-hydroxy-5-methoxypentyl)-N-((R)-1-hydroxy-3-(methylamino) propan-2-yl)piperidine-1-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a solution of (3R)-3-((S)-1-(2-(2-ethylphenoxy)phenyl)-1-hydroxy-5-methoxypentyl)-N-((R)-1-hydroxy-3-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propan-2-yl)piperidine-1-carboxamide (10.0 mg, 0.01 mmol) in acetonitrile (1.0 mL) was added excess tetraethylammonium fluoride. The resulting solution was heated at 50° C. for 2 h, and concentrated under vacuum. The residue was purified by prep HPLC to give (3R)-3-((S)-1-(2-(2-ethylphenoxy)phenyl)-1-hydroxy-5-methoxypentyl)-N-((R)-1-hydroxy-3-(methylamino) propan-2-yl)piperidine-1-carboxamide (2 mg) as its TFA salt. 1H NMR (400 MHz, CD3OD) 7.62 (d, 1 H), 7.32 (d, 1 H), 7.04-7.20 (m, 4 H), 6.74 (d, 1 H), 6.56 (d, 1 H), 4.40 (d, 1 H), 4.00 (m, 1 H), 3.92 (d, 1 H), 3.60 (m, 1 H), 3.54 (m, 1 H), 3.26 (t, 2 H), 3.24 (s, 3 H), 3.22 (m, 1 H), 3.04 (m, 1 H), 2.82 (m, 1 H), 2.64 (s, 3 H), 2.62 (q, 2 H), 2.42 (m, 2 H), 1.94 (m, 1 H), 1.24-1.64 (m, 7 H), 1.08 (t, 3 H), 0.98 (m, 1 H); MS m/z 528 (M+H+).

Provenance & Evidence