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 419691Notes

Reaction equation

HRID 419691 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-6391a9b8a67b4bb797cf2510573a7bbe
Source dataset
uspto-grants-2012_01
Patent number
US08093392B2

Reaction notes

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