反应详情

To a solution of methyl 3-(3-nitrophthalimido)-3-(3-ethoxy-4-methoxyphenyl)propionate (2.5 g, 5.8 mmol) in 25 mL of ethyl acetate was added 0.25 g of 10% palladium on carbon catalyst. The mixture was hydrogenated in a Parr-Shaker apparatus at 55-60 psi of hydrogen overnight. The reaction mixture was filtered through celite and the filtrate was concentrated in vacuo to afford a yellow solid. The crude product was purified by flash column chromatography (silica gel, 7% ethyl acetate/methylene chloride). The resulting solid was recrystallized (60 mL ethyl acetate/20 mL hexane) and was then dried in vacuo (60° C., <1 mm) to afford 1.28 g (55%) of methyl 3-(3-aminophthalimido)-3-(3-ethoxy-4-methoxyphenyl)propionate as a yellow solid: mp 134°-136° C.; 1H NMR (CDCl3) δ 7.40-7.26 (m, 1 H); 7.16-7.01 (m, 3 H), 6.86-6.72 (m, 2 H), 5.71 (dd, J=6, 9.8 Hz, 1 H), 5.28 (br s, 2 H), 4.10 (q, J=7 Hz, 2 H), 3.83 (s, 3 H), 3.73 (dd, J=9.8, 16.5 Hz, 1 H), 3.64 (s, 3 H), 3.24 (dd, J=6, 16.5 Hz, 1 H), 1.44 (t, J=7 Hz, 3 H); 13C NMR (CDCl3) δ 171.1, 169.8, 168.3, 148.9, 148.1, 145.3, 134.9, 132.3, 131.3, 120.9, 120.0, 112.5, 112.4, 111.1, 110.8, 64.2, 55.8, 51.8, 50.2, 36.0, 14.6; HPLC (Waters Nova-Pak C18 column, 3.9×150 mm, 4 micron, 1 mL/min, 240 nm, 50/50, acetonitrile/0.1% aqueous phosphoric acid) 5 min, 100%; Anal. Calcd. for C21H22N2O6. Theoretical: C, 63.31, H, 5.57, N, 7.03. Found: C, 63.11; H, 5.50; N, 6.99.

1. filtrationThe reaction mixture was filtered through celite
2. concentrationthe filtrate was concentrated in vacuo
3. customto afford a yellow solid
4. customThe crude product was purified by flash column chromatography (silica gel, 7% ethyl acetate/methylene chloride)
5. customThe resulting solid was recrystallized (60 mL ethyl acetate/20 mL hexane)
6. customwas then dried in vacuo (60° C., <1 mm)