Sodium hydride → (2S)-2-[1-(3-chloro-benzyl)-2-oxo-1,4-dihydro-2H-quinazolin-3-yl]-3-Methyl-butyric acid tert-butyl ester

HRID 2065499Notes

Reaction equation

HRID 2065499 reaction equation
[C:1]([O:5][C:6](=[O:22])[C@@H:7]([N:11]1[CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][C:12]1=[O:21])[CH:8]([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2].[Cl:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH2:27]Br.[H-].[Na+]>CS(C)=O>[C:1]([O:5][C:6](=[O:22])[C@@H:7]([N:11]1[CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([CH2:27][C:26]2[CH:29]=[CH:30][CH:31]=[C:24]([Cl:23])[CH:25]=2)[C:12]1=[O:21])[CH:8]([CH3:10])[CH3:9])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 66650119(2S)-3-Methyl-2-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-butyric acid tert-butyl ester

Product 1

HCID 53628862(2S)-2-[1-(3-chloro-benzyl)-2-oxo-1,4-dihydro-2H-quinazolin-3-yl]-3-Methyl-butyric acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a mixture of (2S)-3-methyl-2-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-butyric acid tert-butyl ester (633 mg, 2.08 mmol) and 3-chlorobenzyl bromide (470 mg, 2.29 mmol) in DMSO (10 mL) was added sodium hydride (75 mg, 1.87 mmol) and the reaction mixture was stirred at room temperature for 40 hours. To this reaction was then added sat. aq. NH4Cl and the mixture was extracted with ethyl acetate. The organic phase was dried (MgSO4), filtered and evaporated.

Workup

  1. extractionadded sat. aq. NH4Cl and the mixture was extracted with ethyl acetate
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-c9f12b35b6e54a0fadefdc3c0abe4be1
Source dataset
uspto-grants-2012_10
Patent number
US08288537B2

Reaction notes

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