反应详情

温度

0 °C

N-Cbz-7-aminonaphthalene-2-sulfonic acid-[1-(5-cyanothiophen-3-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]amide (0.56 g, 1.01 mmol) is dissolved in 10 mL of DMF and cooled to 0° C. Sodium hydride (42 mg of a 60% dispersion in mineral oil, 1.06 mmol) is added and the solution is stirred for 20 minutes. To the mixture is added benzyl bromide (0.18 g, 1.06 mmol). The reaction mixture is stirred at 0° C. for 20 minutes and then at room temperature for 1.5 hours. The solution is poured into a separatory funnel and diluted with 100 mL of EtOAc. The organic layer is washed with water, 1 N HCl and saturated NaCl solution, then dried over MgSO4, filtered and concentrated. The crude residue is purified by column chromatography eluting with a gradient of 25% EtOAc/CH2Cl2 to 50% EtOAc/CH2Cl2 to give the title compound (0.34 g, 0.53 mmol) as a solid.

1. stirringThe reaction mixture is stirred at 0° C. for 20 minutes
2. waitat room temperature for 1.5 hours
3. additionThe solution is poured into a separatory funnel
4. washThe organic layer is washed with water, 1 N HCl and saturated NaCl solution
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. customThe crude residue is purified by column chromatography
9. washeluting with a gradient of 25% EtOAc/CH2Cl2 to 50% EtOAc/CH2Cl2