Reaction Steps
A solution of diethyl N-(4-((1,2-dihydro-3-methyl-1-oxobenzo[f]quinazolin-9-yl)sulfonamido)benzoyl)-L-glutamate (0.22 g, 0.37 mmol) in ethanol (3 ml) and 0.25 N NaOH (12 ml) was stirred at room temperature for 3 hours. The solution was slowly acidified to pH 3 with 1N HCl and the resulting precipitate filtered, washed with water, and dried under high vacuum to give N-(4-((1,2-dihydro-3-methyl-1-oxobenzo[f]quinazolin-9-yl)sulfonamido)benzoyl)-L-glutamic acid as a white solid (0.20 g). 1H NMR (DMSO-d6, 200 MHz) δ: 1.73-2.15 (m, 2H, gluCH2), 2.27 (t, J=7 Hz, 2H, gluCH2), 2.43 (s, 3H, CH3), 4.22-4.36 (m, 1H, gluCH), 7.20 (d, J=9 Hz, 2H, Ar), 7.69 (d, J=9 Hz, 2H, Ar), 7.76 (d, J=9 Hz, 1H, Ar), 7.90 (dd, J=9, 2 Hz, 1H, Ar), 8.18 (d, J=9 Hz, 1H, Ar), 8.28 (d, J=9 Hz, 1H, Ar), 8.39 (d, J=8 Hz, 1H, gluNH), 10.44 (d, J=2 Hz, 1H, Ar), 10.86 (br s, 1H, SO2NH), 12.32 (br s, 2H, CO2H's), 12.75 (br s, 1H, N2H). Anal. Calculated for C25H22N4O8S.4/5H2O): C, 54.30; H, 4.30; N, 10.13; S. 5.80. Found: C, 54.29; H, 4.25; N, 10.13; S. 5.72.
