Sodium Hydroxide → [4-(1-tert-butoxycarbonylmethyl-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-phenyl]-acetic acid
Reaction equation
C([O:3][C:4](=[O:32])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:13]2=[O:31])=[CH:8][CH:7]=1)C.[OH-].[Na+]>CO>[C:27]([O:26][C:24]([CH2:23][N:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:21](=[O:22])[N:12]([C:9]2[CH:8]=[CH:7][C:6]([CH2:5][C:4]([OH:32])=[O:3])=[CH:11][CH:10]=2)[C:13]1=[O:31])=[O:25])([CH3:30])([CH3:28])[CH3:29]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of [4-(1-tert-butoxycarbonylmethyl-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-phenyl]-acetic acid ethyl ester (Intermediate G) (1.4 g, 3.2 mmol) in MeOH (25 ml) is treated with aqueous sodium hydroxide (0.5 M, 10 ml). After stirring at RT for 30 minutes, the MeOH is removed in vacuo and the resulting mixture is diluted with distilled water and washed with EtOAc (2×) to remove impurities. The separated aqueous phase is acidified with dilute HCl (0.1 M) to pH 3 and extracted with EtOAc (2×). The combined organic portions are dried over MgSO4, filtered and concentrated in vacuo to afford the title compound as an off-white solid.