Diisopropylethylamine → HCID 70162399, compound

Participants

Reaction Steps

To a solution of 5-(2-adamantan-1-yl-ethyl)-2-(2-fluoro-phenyl)-1H-imidazole-4-carboxylic acid (Example 50) (200 mg, 0.50 mmol) and β-alanine benzyl ester p-toluenesulfonate (175 mg, 0.50 mmol) in DCM (5 ml) was added N,N-diisopropylethylamine (0.26 ml, 1.50 mmol), 4-dimethylaminopyridine (cat.) and bromo-tris-pyrrolidino-phosphonium hexafluorophosphate (PyBrOP) (230 mg, 0.50 mmol). The solution was kept at room temperature for 16 h, diluted with DCM (10 ml), washed with 5% aqueous potassium hydrogen sulphate and with saturated sodium hydrogen carbonate. The organic phase was dried (MgSO4) and the solvent was evaporated. The residue was purified by flash column chromatography (silica, DCM/ethyl acetate 9:1) to afford the product as colourless foam (153 mg, 58%). 1H NMR (300 MHz, CDCl3) 9.72 (1H, br s), 8.23 (1H, m), 7.68 (1H, t), 7.37-7.15 (8H, m), 5.17 (2H, s), 3.73 (2H, m), 3.07 (2H, m), 2.72 (2H, m), 1.97 (3H, s), 1.73-1.41 (14H, m).

Provenance & Evidence