3-Aminoquinoline → HCID 70207200, compound

Participants

Reaction Conditions

Reaction Steps

A cold solution (0° C.) of N-Boc-phenylalanyl-Nδ-Boc-ornithine (0.2 g, 0.4 mmol), 3-aminoquinoline (0.082 g, 0.57 mmol), diisopropylethylamine (0.103 mg, 0.8 mmol), 4-(dimethylamino)pyridine (5 mg, 0.04 mmol), and methylene chloride (3 mL) was treated dropwise with phosphorus oxychloride (0.5 mmol). The reaction was stirred at 0° C. for 1 hr and ethyl acetate (20 mL) was added. The organic layer was washed with water (2×20 mL), 1N hydrochloric acid (2×10 mL), saturated sodium bicarbonate (2×10 mL) and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and the filtrate adsorbed onto 100 mg of silica gel and applied to a column prepacked with silica gel. The column was eluted with ethyl acetate/hexane (70:30, v:v) to afford titled compound (51 mg) as an oil: 1H NMR (400 MHz, CDCl3) δ1.42-1.55 (18H), 1.6-1.8 (1H), 2.0-2.1 (1H), 3.1-3.2 (4H), 3.3-3.4 (1H), 4.19-4.21 (1H), 4.70-4.80 (1H), 5.0-5.15 (1H), 7.21-7.29 (5H), 7.53-7.55 (1H), 7.63-7.65 (1H), 7.79-7.81 (1H), 8.05-8.07 (1H), 8.74 (1H), 8.94 (1H); mass spectrum (relative intensity) m/e 606 (100, M+1).

Provenance & Evidence