Dimethylformamide → (3-methoxycarbonylmethyl-2-oxo-3,4-dihydro-2H-quinazolin-1-yl)-acetic acid

HRID 472754Notes

Reaction equation

HRID 472754 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][N:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]1=[O:15].C([O-])([O-])=O.[K+].[K+].CN(C=O)C.Br[CH2:29][C:30]([O:32]C(C)(C)C)=[O:31]>O>[CH3:1][O:2][C:3]([CH2:4][N:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:29][C:30]([OH:32])=[O:31])[C:6]1=[O:15])=[O:16]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 68589889HCID 68589889, compound

Product 1

HCID 68590330(3-methoxycarbonylmethyl-2-oxo-3,4-dihydro-2H-quinazolin-1-yl)-acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of (2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-acetic acid methyl ester (9.5 g, 29.3 mmol) and K2CO3 (2.5 eq, 10.31 g, 73.3 mmol) in a round bottom flask are treated with dry DMF. Tert-Butyl bromoacetate (1.02 eq, 4.2 ml, 30 mmol) is added dropwise via syringe under argon. The reaction suspension is stirred at RT for one hour. The reaction mixture is diluted with distilled water and extracted with EtOAc (3×). The separated organic layer is dried over MgSO4, filtered and the solvent concentrated in vacuo. The title compound is obtained as brown viscous oil crystallizing on standing. [M+H]+ 335.

Workup

  1. extractionextracted with EtOAc (3×)
  2. dry with materialThe separated organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationthe solvent concentrated in vacuo

Sources & evidence

ORD record
ord-e1312b9645ae4484bb338e80004f69a6
Source dataset
uspto-grants-2014_01
Patent number
US08633211B2

Reaction notes

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