(R)-cyclohexyl-[1-(1,4-dimethyl-1H-indol-3-ylmethyl)-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-acetic acid methyl ester → (R)-Cyclohexyl-[1-(1,4-dimethyl-1H-indol-3-ylmethyl)-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-acetic acid

HRID 388450Notizen

Reaktionsgleichung

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

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

To a solution of (R)-cyclohexyl-[1-(1,4-dimethyl-1H-indol-3-ylmethyl)-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-acetic acid methyl ester (124 mg, 0.26 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 16 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 3.5% MeOH in dichloromethane as the eluent to afford the title compound. LCMS (ESMS): m/z 460.86 (M+H+)

Aufarbeitung

temperatureto cool to room temperature
customquenched with 4M HCl in dioxane (500 μL)
concentrationis concentrated
customThe resulting residue is purified by flash chromatography with 3.5% MeOH in dichloromethane as the eluent

Quellen und Nachweise

ORD-Eintrag: ord-9cb3b996d5fd410fa90987cfd5656a9e
Quelldatensatz: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08377949B2

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