反应详情

(S)-Pyroglutamic acid methyl ester (0.200 g, 1.40 mmol) was dissolved in dry THF (5 ml) and NaH (0.061 g, 1.5 mmol) was added. After gas evolution ceased, 4-nitrobenzyl bromide (0.332 g, 1.54 mmol) was added and the mixture stirred for 1 h. The reaction was quenched with saturated NaHCO3 solution (40 mL) and extracted with EtOAc (2×50 ml). The organic layers were washed with water, brine, dried (MgSO4), filtered, and concentrated to give the title compound as a solid. 1H NMR (CDCl3) δ 8.19 (d, 2H, J=8.6 Hz), 7.40 (d, 2H, J=8.6 Hz), 5.29 (d, 1H, J=15 Hz), 4.19 (d, 1H, J=15 Hz), 4.02 (dd, 1H, J=3,9 Hz), 3.79 (s, 3H), 2.54-2.67 (m, 1H), 2.42-2.51 (m, 1H), 2.27-2.39 (m, 1H), 2.11-2.21 (m, 1H).

1. customThe reaction was quenched with saturated NaHCO3 solution (40 mL)
2. extractionextracted with EtOAc (2×50 ml)
3. washThe organic layers were washed with water, brine
4. dry with materialdried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated