Trifluoroacetic acid → HCID 58619083, compound

Participants

Reaction Conditions

Reaction Steps

To a round bottom flask equipped with a stirring bar is charged [1,4′]bipiperidinyl-4′-yl-methanol, 22, (2.2 g, 11.1 mmol, 1.0 eq.) 2-(R)-tert-butoxycarbonylamino-3-(4-chlorophenyl)-propionic acid (3.648 g, 12.2 mmol), 1-hydroxybenzotriazole (2.552 g, 18.9 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (3.71 g, 18.9 mmol) in anhydrous N,N-dimethylformamide (80 mL). The mixture is cooled to 0° C. and N,N-diisopropyl-ethylamine (4.1 mL, 37.7 mmol) is added. The ice bath is removed and the reaction mixture allowed to stir overnight. The mixture is concentrated under reduced pressure and purified by preparative HPLC to afford 2.83 g (43% yield) of the desired compound as the trifluoroacetic acid salt. 1H NMR (CD3OD, 300 MHz) δ 0.85–2.13 (m, 19H), 2.65–3.82 (m, 8H), 3.90–4.10 (m, 3H), 4.48 (m, 1H), 4.76 (m, 1H), 7.22–7.48 (m, 4H). MS (ESI) m/z 480 (M+H+).

Provenance & Evidence