(S)-[1-(1,4-dimethyl-1H-indol-3-ylmethyl)-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-phenyl-acetic acid methyl ester → (S)-[1-(1,4-Dimethyl-1H-indol-3-ylmethyl)-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-phenyl-acetic acid

HRID 388461Notes

Reaction equation

C[O:2][C:3](=[O:35])[C@@H:4]([N:11]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([CH2:22][C:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][C:30]=3[CH3:32])[N:25]([CH3:33])[CH:24]=2)[C:12]1=[O:34])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>O1CCOCC1.O>[CH3:33][N:25]1[C:26]2[C:31](=[C:30]([CH3:32])[CH:29]=[CH:28][CH:27]=2)[C:23]([CH2:22][N:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:20](=[O:21])[N:11]([C@@H:4]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:3]([OH:35])=[O:2])[C:12]2=[O:34])=[CH:24]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of (S)-[1-(1,4-dimethyl-1H-indol-3-ylmethyl)-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-phenyl-acetic acid methyl ester (100 mg, 0.21 mmol) in dioxane (2.5 ml) is added a solution of LiOH monohydrate (25 mg, 0.60 mmol) in H2O (2.5 mL). The solution is stirred at 60° C. for 4 hours. The reaction mixture is allowed to cool to room temperature, quenched with 4M HCl in dioxane (500 μL) and is concentrated. The resulting residue is purified by flash chromatography with 10% MeOH in dichloromethane as the eluent to afford the title compound. LCMS (ESMS): m/z 454.19 (M+H+).

Workup

temperatureto cool to room temperature
customquenched with 4M HCl in dioxane (500 μL)
concentrationis concentrated
customThe resulting residue is purified by flash chromatography with 10% MeOH in dichloromethane as the eluent

Sources & evidence

ORD record: ord-223c97516fce4dc1a93bb29779904648
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08377949B2

Reaction notes

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