octanedioic acid [4-(3-Nitro-phenyl)-thiazol-2-yl]-amide methyl ester → octanedioic acid [4-(3-Amino-phenyl)-thiazol-2-yl]-amide methyl ester

Participants

Reaction Steps

A suspension of compound 14 (0.391 g, 1 mmol) and Pd/C (10 wt. %, 50 mg) in EtOH and AcOH (20 ml+1 ml) was reacted under hydrogen atmosphere at 50° C. for 2 hours. The catalyst was removed by filtration through a pad of Celite. After removal of the solvent in vacuo, the crude material was dissolved in EtOAc and washed with NaHCO3 solution and brine and dried over Na2SO4. The solvent was removed by rotary evaporation. The crude solid was purified by flash chromatography (EtOAc/hexane, 2:1) to give compound 20 (0.261 g, 72.4%). 1H NMR (300 MHz, CDCl3) δ 11.2 (1H, s), 7.22 (1H, s), 7.20 (1H, s), 7.16 (1H, brs), 7.10 (1H, s), 6.70-6.66 (1H, m), 3.69 (3H, s), 2.28 (2H, t, J=7.4 Hz), 2.06 (2H, dd, J=7.3, 4.7 Hz), 1.61-1.45 (4H, m), 1.22-1.08 (4H, m). 13C NMR (75 MHz, CDCl3) δ 174.6, 171.8, 159.6, 150.1, 147.3, 135.7, 130.2, 116.9, 115.3, 113.0, 108.1, 51.9, 36.1, 34.3, 29.07, 29.01, 25.09, 25.00, 21.4.

Provenance & Evidence