Lipoic acid → 5-[1,2]dithiolan-3-yl-pentanoic acid {6-[Ethyl-(2-methoxy-benzyl)-amino]-hexyl}-amide

Participants

Reaction Steps

It was synthesized from N1-ethyl-N1-(2-methoxy-benzyl)-hexane-1,6-diamine (patent application PCT/IT03/0227) (300 mg, 1.13 mmol) and lipoic acid (350 mg, 1.70 mmol) following the procedure described for 17, and purified by gravity column. Elution with a gradient of mobile phase petroleum ether/toluene/CH2Cl2/EtOH/aqueous 30% ammonia solution (7:2:1:1:0.05 to 7:1:1:1:0.5) afforded 18 as a waxy solid: 43% yield, 1H NMR (200 MHz, CDCl3) δ 7.42-7.48 (m, 1H); 7.18-7.26 (m, 1H), 6.85-6.99 (m, 2H), 5.43 (br t, 1H, exchangeable with D2O), 3.84 (s, 3H), 3.53-3.64 (m, 1H+s, 2H), 3.08-3.27 (m, 4H), 2.43-2.57 (m, 5H), 2.17 (t, J=7.4 Hz, 2H), 1.82-2.00 (m, 1H), 1.29-1.73 (m, 14H), 1.07 (t, J=7.0 Hz, 3H); MS (ESI+) m/z 453 (M+H)+. Anal. Calculated for C24H40N2O2S2: C, 63.67; H, 8.91; N, 6.19. Found: C, 63.79; H, 8.93, N, 6.17.

Provenance & Evidence