Water → (S)-2-(4-(((4-oxo-3,4-dihydroquinazolin-6-yl)methyl)(prop-2-ynyl)amino)benzamido)pentanedioic acid

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Reaction Steps

A mixture of the gummy triester (5)(0.633 g, 0.001 mole), H2O (18 mL), EtOH (18 mL), and 1.00N NaOHaq (5 mL, 0.005 mole) was placed in a conical flask and stirred vigorously (magnetic stirrer) for 40 minutes to give a pale yellow solution. This solution was kept at 22° C. for 18.5 hours. It was then filtered through a bed of Celite (carbon treatment) and the clear filtrate acidified to pH 2.5 with 1.00 N HClaq. The resulting white gelatinous precipitate of the product was centrifuged (1500g/30 minutes) and washed by three cycles of resuspension (H2 0: 80 mL, 80 mL, and 40 mL)--centrifugation--decantation. The pellet was dried in vacuo over P2 05 --first at 22° C./24 hours in a desiccator and then at 80° C./4 hours in a pistol. A pale yellow amorphous solid was obtained (0.312 g, 67.5%),

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