(S)-2-[1-(1,4-dimethyl-1H-indol-3-ylmethyl)-6-methoxy-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-hexanoic acid methyl ester → (S)-2-[1-(1,4-Dimethyl-1H-indol-3-ylmethyl)-6-methoxy-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-hexanoic acid

HRID 388482Notes

Reaction equation

C[O:2][C:3](=[O:35])[C@@H:4]([N:9]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:20][CH3:21])[CH:16]=2)[N:11]([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:10]1=[O:34])[CH2:5][CH2:6][CH2:7][CH3:8]>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:11]2[C:12]3[C:17](=[CH:16][C:15]([O:20][CH3:21])=[CH:14][CH:13]=3)[C:18](=[O:19])[N:9]([C@@H:4]([CH2:5][CH2:6][CH2:7][CH3:8])[C:3]([OH:35])=[O:2])[C:10]2=[O:34])=[CH:24]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of (S)-2-[1-(1,4-dimethyl-1H-indol-3-ylmethyl)-6-methoxy-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-hexanoic acid methyl ester (124 mg, 0.26 mmol) in dioxane (2.5 ml) is added a solution of LiOH monohydrate (50 mg, 1.19 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 concentrated. The resulting residue is triturated with H2O and MeOH to afford the title compound. LCMS (ESMS): m/z 464.87 (M+H+)

Workup

temperatureto cool to room temperature
customquenched with 4M HCl in dioxane (500 μL)
concentrationconcentrated
customThe resulting residue is triturated with H2O and MeOH

Sources & evidence

ORD record: ord-cd2722c53e9a4cbcbaa806777ebea81c
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08377949B2

Reaction notes

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