7-(2-Methyl-1,3-dioxolan-2-yl)-1-(4-(2-naphthyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)heptan-1-one → 1-[5-(2-Naphthyl)-1H-imidazol-2-yl]nonane-1,8-dione

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Reaction Steps

The ketone E3 was dissolved in TFA/DCM (1:1) and stirred for 4 hr at RT. After evaporation of the solvent under reduced pressure, the crude product was purified by preparative RP-HPLC (column: C18), using H2O (0.1% TFA) and MeCN (+0.1% TFA) as eluents. The desired fractions were lyophilized to afford E4 as a white solid. 1H NMR (300 MHz, DMSO) δ: 8.17 (1H, s), 7.92-7.79 (3H, m), 7.76-7.64 (2H, m), 7.55-7.45 (2H, m), 3.15 (2H, t, J=7.4 Hz), 2.44 (2H, t, J=7.4 Hz), 2.15 (3H, s), 1.74 (2H, m), 1.58 (2H, m), 1.37 (4H, m). MS (ES) C22H24N2O2 requires: 348, found: 349 (M+H)+.

Provenance & Evidence