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

HRID 885250Notes

Reaction equation

HRID 885250 reaction equation
[O:1]1[CH2:5][C:4](=O)[N:3]=[C-:2]1.[H-].[Na+].[CH3:9][O:10][C:11](=[O:29])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]2[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][C:21]=2[CH2:27]Br)[CH:14]=1.Cl.[O:31]1CCOCC1>CCOC(C)=O>[CH3:9][O:10][C:11](=[O:29])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]2[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][C:21]=2[CH2:27][N:3]2[CH2:4][CH2:5][O:1][C:2]2=[O:31])[CH:14]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 312751,4-DioxaneHCID 532495662H-1,3-oxazol-2-id-4-oneHCID 58237479[3-(4-Bromo-2-bromomethyl-phenoxy)-phenyl]acetic acid methyl ester

Product 1

HCID 58237622{3-[4-Bromo-2-(2-oxo-oxazolidin-3-ylmethyl)-phenoxy]-phenyl}-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 2-oxazolidone (0.69 g, 8.0 mmol) in 1,4-dioxane (30 mL) under N2 was added sodium hydride (60% in mineral oil; 0.38 g, 9.4 mmol). After stirring for 15 minutes, [3-(4-bromo-2-bromomethyl-phenoxy)-phenyl]-acetic acid methyl ester (3 g, 7.2 mmol) was added, and the reaction was stirred for 24 hours at room temperature. Once no starting material was seen by analytical LCMS, the mixture was worked-up with 10% aqueous HCl and EtOAc, and the crude material was purified by silica gel chromatography to give the desired product as a colorless oil (2 g).

Workup

  1. stirringthe reaction was stirred for 24 hours at room temperature
  2. customthe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-f211314c265d48598306beab423db8ba
Source dataset
uspto-grants-2012_08
Patent number
US08242145B2

Reaction notes

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