Sodium Bicarbonate → HCID 21248818, compound

Participants

Reaction Steps

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).

Provenance & Evidence