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

HRID 472754Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 472754
[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]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-e1312b9645ae4484bb338e80004f69a6
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633211B2

Notizen zur Reaktion

Wird geladen…