Dimethylformamide → {3-[4-Bromo-2-(2-oxo-oxazolidin-3-ylmethyl)-phenoxy]-phenyl}-acetic acid ethyl ester

HRID 885236

Reaktionsgleichung

Reaktionsgleichung von HRID 885236
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:14]=2[CH2:20]Br)[CH:7]=1)[CH3:2].[O:23]1[CH2:27][C:26](=O)[N:25]=[C-:24]1.[H-].[Na+].CN(C=[O:35])C>>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:14]=2[CH2:20][N:25]2[CH2:26][CH2:27][O:23][C:24]2=[O:35])[CH:7]=1)[CH3:2]

Komponenten

5

Edukt 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 532495662H-1,3-oxazol-2-id-4-oneHCID 58237602[3-(4-Bromo-2-bromomethyl-phenoxy)-phenyl]-acetic acid ethyl ester

Produkt 1

HCID 58237550{3-[4-Bromo-2-(2-oxo-oxazolidin-3-ylmethyl)-phenoxy]-phenyl}-acetic acid ethyl ester

Versuchsvorschrift

To [3-(4-bromo-2-bromomethyl-phenoxy)-phenyl]-acetic acid ethyl ester (0.40 g, 0.93 mmol) and 2-oxazolidone (0.10 g, 1.14 mmol) in DMF (5 mL) was added sodium hydride (60% in mineral oil; 0.05 g, 1.25 mmol), and the mixture was stirred at room temperature for 30 minutes. After work-up, the crude material was purified by silica gel chromatography (0-50% EtOAc in hexanes). Further purification by preparative HPLC gave the desired product (0.02 g).

Aufarbeitung

  1. customAfter work-up, the crude material was purified by silica gel chromatography (0-50% EtOAc in hexanes)
  2. customFurther purification by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-ee687218aa6f4af1baccdc971357a00c
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08242145B2

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