Hydrochloric Acid → N-(4-(((3-amino-1,2-dihydro-1-oxobenzo[f]quinazolin-9-yl)-amino)sulfonyl)benzoyl)-L-glutamic acid

Participants

Reaction Conditions

Reaction Steps

A solution of diethyl N-(4-(((3-amino-1,2-dihydro-1-oxobenzo[f]quinazolin-9-yl)amino)sulfonyl)benzoyl)-L-glutamate (0.175 g, 0.3 mmoles) in 1 N NaOH (12 ml) was stirred and heated to 50° C. under a nitrogen atmosphere for 24 hrs. After cooling,the solution was acidified (pH 3) with concentrated HCl to cause precipitation of the product which was filtered, washed with water and dried to give N-(4-(((3-amino-1,2-dihydro-1-oxobenzo[f]quinazolin-9-yl)-amino)sulfonyl)benzoyl)-L-glutamic acid as an off-white solid. (0.18 g, 99%) 1H NMR (DMSO-d6, 300 MHz) δ: 1.81-2.13 (m, 2H, glu-CH2); 2.32 (t, J=7.6 Hz, 2H, glu-CH2); 4.34 (m, 1H, glu-CH); 6.58 (br s, 2H, NH2); 7.16 (d, J=8.9 Hz, 1H, Ar); 7.22 (dd, J=8.6, 2 Hz, 1H, Ar); 7.74 (d, J=8.7 Hz, 1H, Ar); 7.89 (d, J=9.0 Hz, 1H, Ar); 7.96 (m, 4H, Ar); 8.78 (d, J=7.6 Hz, 1H, glu-NH); 9.49 (d, J=2 Hz, 1H, Ar); 10.68 (s, 1H, NH); 11.1 (br s, 1H, NH); 12.3 (br s, 2H, (CO2H)2). Anal. Calculated for C24H21N5O8S.3H2O: C, 48.56; H, 4.58; N, 11.80; S, 5.40. Found: C, 48.38; H, 4.30; N, 11.69; S. 5.34.

Provenance & Evidence