Lipoic acid → N-[3-[3-[1-(Dimethylamino)ethyl]phenoxy]propyl]-1,2-dithiolane-3-pentanamide

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Reaction Steps

5-[1,2]dithiolan-3-yl-pentanoic acid {3-[3-(1-dimethylamino-ethyl)-phenoxy]-propyl}-amide (19) was synthesized from 19c (150 mg, 0.67 mmol) and lipoic acid (210 mg, 1.02 mmol) following the procedure described for 17, and purified by gravity column. Elution with petroleum ether/toluene/CH2Cl2/MeOH/aqueous 30% ammonia solution (6:1:1.5:1.5:0.01) afforded 19 as a waxy solid; 30% yield, 1H NMR (200 MHz, CDCl3) δ 7.27 (t, J=8.2 Hz, 1H); 6.78-6.98 (m, 3H), 5.99 (br t, 1H); 4.09 (t, J=6.0 Hz, 2H); 3.21-3.62 (m, 5H), 3.05-3.19 (m, 3H), 2.40-2.53 (m, 1H), 2.32 (s, 6H), 2.22 (t, J=7.2 Hz, 2H); 1.81-2.0 (m, 3H), 1.65-1.73 (m, 4H), 1.47 (d, J=6.6 Hz, 3H); MS (ESI+) m/z 411 (M+H)+. Anal. Calculated for C21H34N2O2S2: C, 61.42; H, 8.35; N, 6.82. Found: C, 61.62; H, 8.36, N, 6.80.

Provenance & Evidence