反应详情

A suspension of diethyl (S)-2-(4-nitrophthalimido)glutarate (35.6 g, 94.1 mmol) and 10% palladium on carbon (0.5 g) (Aldrich) in ethanol (200 ml) was shaken under a hydrogen atmosphere (40-50 psi) for 26 hours. The solution was filtered through celite and concentrated in vacuo. The residue was purified by chromatography on silica gel (250 g) eluting with diethyl ether:hexane (4:1) to give diethyl (S)-2-(4-aminophthalimido)glutarate as a viscous yellow oil (29.1 g). 1H NMR (DMSO-d6, 300 MHz) δ: 1.10 (t, J=7 Hz, 3H, ester CH3), 1.12 (t, J=7 Hz, 3H, ester CH3), 2.17-2.39 (m, 4H, glu CH2CH2), 3.87-3.98 (m, 2H, ester CH2), 4.05-4.18 (m, 2H, ester CH2), 4.75-4.82 (m, 1H, glu CH), 6.57 (br s, 2H, NH2) 6.82 (dd, J=8,2 Hz 1H Ar) 6.93 (d, J=2 Hz, 1H, Ar), 7.51 (d, J=8 Hz, 1H, Ar). Mass spectrum (CI-CH4) 349 (M+1, 40.8%), 303 (60.1%), 275 (100%). Anal Calculated for C17H20N2O6 : C, 58.62; H, 5.79; N, 8.04. Found: C, 58.62; N, 5.80; N, 8.00.

1. filtrationThe solution was filtered through celite and
2. concentrationconcentrated in vacuo
3. customThe residue was purified by chromatography on silica gel (250 g)
4. washeluting with diethyl ether:hexane (4:1)