反应详情

A solution of chloromethylchlorosulphate (2.21 g) in dichloromethane (5 ml) was added dropwise to a stirred mixture of 4-[N-(4-nitrobenzyloxycarbonyl)glycylamino]-benzoic acid (4.00 g), sodium bicarbonate (3.00 g) and tetrabutylammonium hydrogen sulphate (0.493 g) in dichloromethane-water (1:1, 50 ml). The mixture was stirred at room temperature for 3 h. The organic phase was separated and the aqueous phase washed with dichloromethane (50 ml). The combined organic extracts were dried (MgSO4), concentrated to low volume and applied to a column of Kieselgel 60. Elution with 50% ethyl acetate/hexane afforded the title compound as a white solid (46%); m.p. 163°-5° (ethyl acetate), (Found: C, 51.49; H, 3.79; N, 9.76. C18H16N3O7Cl requires C, 51.26; H, 3.82; N, 9.96%); νmax (Nujol) 3400, 3300, 1740, 1685, and 1610 cm-1 ; δH (CDCl3 /D6 -DMSO) 3.95 (2H, d, J 6.0 Hz), 5.25 (2H, s), 5.97 (2H, s), and 7.35-8.20 (10H, m).

1. customThe organic phase was separated
2. washthe aqueous phase washed with dichloromethane (50 ml)
3. dry with materialThe combined organic extracts were dried (MgSO4)
4. concentrationconcentrated to low volume
5. washElution with 50% ethyl acetate/hexane