反应详情

A mixture of 1-methyl-5-nitro-3-phenyl-1H-indole-2-carboxylic acid (0.56 g, 1.9 mmol), 1-[3-(dimethylamino)propyl-3-ethylcarbodiimide hydrochloride (0.47 g, 2.5 mmol), and L-leucine methyl ester hydrochloride (0.40 g, 2.2 mmol) was stirred in CH2Cl2 (20 mL). N-methylmorpholine (1.01 g, 10 mmol) was added and the mixture was stirred at room temperature overnight. The mixture was then washed with 0.05 N HCl and water. The resulting solution was dried with MgSO4 and concentrated. The residue was dissolved in 30 mL of ethanol and a large excess of Raney® nickel and hydrazine (0.6 mL, 19 mmol) were added. After stirring at room temperature for 2 h the catalyst was then removed by filtering through a short pad of Celite®521. The filtrate was concentrated to give 0.65 g (87%) of crude methyl N-[(5-amino-1-methyl-3-phenyl-1H-indol-2-yl)carbonyl]-L-leucinate as a pale yellow solid: MS (ESI) m/z 394 (MH+); HRMS calcd for C23H28N3O3: 394.2128; found (ESI+): 394.2121.

1. washThe mixture was then washed with 0.05 N HCl and water
2. dry with materialThe resulting solution was dried with MgSO4
3. concentrationconcentrated
4. dissolutionThe residue was dissolved in 30 mL of ethanol
5. stirringAfter stirring at room temperature for 2 h the catalyst
6. customwas then removed
7. filtrationby filtering through a short pad of Celite®521
8. concentrationThe filtrate was concentrated