Hydrochloric Acid → (2S)-2-[5-[[(1,2-Dihydro-3-methyl-1-oxobenzo[f]quinazolin-9-yl)methyl]amino]-1,3-dihydro-1-oxo-2H-isoindol-2-yl]pentanedioic acid

Participants

Reaction Steps

A solution of diethyl (S)-2-(5-(((1,2-dihydro-3-methyl-1-oxo-benzo-[f]quinazolin-9-yl)methyl)amino)-1-oxo-2-isoindolinyl)glutarate (3.20 g, 5.75 mmol) in 0.2N NaOH (140 ml) was stirred under nitrogen for 3 hours at room temperature. The solution was then slowly adjusted to pH 3 with 1N HCl and the resulting suspension allowed to stir briefly. The white solid was filtered under nitrogen, washed with water, and dried under high vacuum to give (S)-2-(5-(((1,2-dihydro-3-methyl-1-oxobenzo[f]quinazolin-9-yl)methyl)amino)-1-oxo-2-isoindolinyl) glutaric acid (2.85 g). 1H NMR (DMSO-d6 /D2O, 300 MHz) δ: 1.86-2.34 (m, 4H, glu CH2CH2), 2.44 (s, 3H, CH3), 4.25 (very strong y coupled AB pair, 2H, glu NCH2Ar), 4.58 (s, 2H, C9 --CH2), 4.67-4.75 (m, 1H, glu CH), 6.69-6.77 (m, 2H, Ar), 7.37 (d, J=8 Hz, 1H, Ar), 7.59 (d, J=9 Hz, 1H, Ar), 7.64 (dd, J=8,2 Hz, 1H, Ar), 8.01 (d, J=8 Hz, 1H, Ar), 8.22 (d, J=9 Hz, 1H, Ar), 9.85 (s, 1H, Ar). Anal. Calculated for C27H24N4O6.1.6H2O: C, 61.27; H, 5.18; N, 10.58. Found: C, 61.29; H, 5.18; N, 10.57.

Provenance & Evidence