Hydrochloric Acid → N1-(4-(3-aminophenyl)thiazol-2-yl)-N8-hydroxyoctanediamide

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a solution of hydroxylamine hydrochloride (0.958 g, 13.8 mmol) in MeOH-KOH (0.772 g, 13.8 mmol) was added at 40° C. for 10 minutes. The reaction mixture was cooled to 0° C. and filtered. Compound 20 (0.250 g, 0.69 mmol) was added to the filtrate followed by KOH (50 mg, 0.89 mmol) at room temperature. After 2 hours, water (20 ml) was added, followed by 1 N HCl until pH reached 6.5. The reaction mixture was extracted with EtOAc, and organic layer was washed with brine, dried over Na2SO4 and filtered. The solvent was removed by rotary evaporation. The crude solid was purified by preparative HPLC to give compound 23 (0.110 g, 43.9%). 1H NMR (300 MHz, CD3OD) δ 7.98 (1H, d, J=7.8 Hz), 7.90 (1H, s), 7.55 (1H, t, J=7.8 Hz), 7.51 (1H, s), 7.29 (1H, dd, J=7.8, 1.2 Hz), 2.51 (2H, t, J=7.2 Hz), 2.11 (2H, t, J=7.2 Hz), 1.74 (2H, t, J=7.0 Hz), 1.65 (2H, t, J=7.0 Hz), 1.50-1.35 (4H, m). 13C NMR (100 MHz, CD3OD) δ 172.1, 158.0, 147.4, 136.3, 129.7, 125.1, 120.8, 119.2, 108.5, 34.6, 28.0, 27.9, 24.7, 24.3.

Herkunft & Nachweise