Lithium Hydroxide → (R)-2-[2,4-Dioxo-1-(1,4,6-trimethyl-1H-indol-3-ylmethyl)-1,4-dihydro-2H-quinazolin-3-yl]-pentanoic acid

HRID 388474Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of (R)-2-[2,4-dioxo-1-(1,4,6-trimethyl-1H-indol-3-ylmethyl)-1,4-dihydro-2H-quinazolin-3-yl]-pentanoic acid methyl ester (50 mg, 0.11 mmol) in 1,4-dioxane (10 mL) and water (2 mL) is added LiOH (5.4 mg, 0.22 mmol) at room temperature. The solution is stirred at 60° C. for 4 hours. The solution is concentrated and water is added to the residue. The solution is acidified by 12N HCl in an ice-bath. The precipitated white solid is collected by filtration and is dried under vacuum to afford the title product. : LCMS (ESMS): m/z 434.89 (M+H+).

Workup

concentrationThe solution is concentrated
additionwater is added to the residue
customThe solution is acidified by 12N HCl in an ice-bath
filtrationThe precipitated white solid is collected by filtration
customis dried under vacuum

Sources & evidence

ORD record: ord-8490a790757f4740a2783aaf801b6ba1
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08377949B2

Reaction notes

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