反应详情

To a solution of L-glutamic acid diethyl ester (0.81 g, 4.0 mmoles) and 4-(((3-amino-1,2-dihydro-1-oxobenzo[f]quinazolin-9-yl)amino)sulfonyl)benzoic acid (0.43 g, 0.9 mmoles) in dry dimethylformamide (20 ml) was added 1-hydroxybenzotriazole monohydrate (0.43 g, 3.2 mmoles) and dicyclohexylcarbodiimide (0.66 g, 3.2 mmoles). The solution was stirred at room temperature under a nitrogen atmosphere for 20 hrs, after which time the solvent was removed under reduced pressure. The residue was recrystallized successively from methylene chloride:methanol/9:1 and methanol to give diethyl N-(4-(((3-amino-1,2-dihydro-1-oxobenzo[f]quinazolin-9-yl)amino)sulfonyl)benzoyl)-L-glutamate as a white solid. (0.215 9, 36%). 1HNMR(DMSO-d6, 300 MHz) δ: 1.12(t, J=7 Hz, 3H, ester-CH3); 1.15(t, J=7 Hz, 3H, ester-CH3); 1.89-2.13(m, 2H, glu-CH2); 2.40(t, J=7.6 Hz, 2H, glu-CH2); 4.00(q, J=7 Hz, 2H, ester-CH2); 4.08(q, J=7 Hz, 2H, ester-CH2); 6.55(br s, 2H, NH2); 7.16(d, J=8.9 Hz, 1H, Ar); 7.23(dd, J=8.7, 2 Hz, 1H, Ar); 7.73(d, J=8.7 Hz, 1H, Ar); 7.89(d, J=8.9 Hz, 1H, Ar); 7.96(m, 4H, Ar); 8.89(d, J=7.4 Hz, 1H, glu-NH); 9.48(d, J=2 Hz, 1H, Ar); 10.67(s, 1H, NH); 11.08(s, 1H, NH). Anal. Calculated for C28H29N5O8S: C, 56.46; H, 4.91; N, 11.76; S. 5.38. Found: C, 56.45; H, 4.94; N, 11.75; S, 5.43.

1. customafter which time the solvent was removed under reduced pressure
2. customThe residue was recrystallized successively from methylene chloride