Hydrochloric Acid → (R)-2-methoxy-4-(4-methyl-2-oxooxazolidin-3-yl)benzoic acid
Reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([N:13]2[C@H:17]([CH3:18])[CH2:16][O:15][C:14]2=[O:19])[CH:10]=[CH:9][C:4]=1[C:5]([O:7]C)=[O:6].[OH-].[Na+].Cl>CO.O1CCCC1>[CH3:1][O:2][C:3]1[CH:12]=[C:11]([N:13]2[C@H:17]([CH3:18])[CH2:16][O:15][C:14]2=[O:19])[CH:10]=[CH:9][C:4]=1[C:5]([OH:7])=[O:6]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a mixture of methyl 4-bromo-2-methoxybenzoate (5.8 mL), (R)-4-methyloxazolidin-2-one (2 g) described in Preparation Example 25, potassium carbonate (2.8 g) and copper (I) iodide (760 mg) were added toluene (10 mL) and N,N′-dimethylethylenediamine (880 μL), and the mixture was refluxed for 8 hr. After cooling, water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and the solvent was evaporated. The residue was purified by column chromatography (hexane:ethyl acetate) to give methyl (R)-2-methoxy-4-(4-methyl-2-oxooxazolidin-3-yl)benzoate (2.1 g). Methyl (R)-2-methoxy-4-(4-methyl-2-oxooxazolidin-3-yl)benzoate (2.1 g) was dissolved in methanol (8 mL) and tetrahydrofuran (8 mL), 1N aqueous sodium hydroxide solution (16 mL) was added, and the mixture was stirred at room temperature for 3 hr. 1N hydrochloric acid (16 mL) was added, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and the solvent was evaporated. The title compound (2.2 g) was obtained.
Workup
- extractionthe mixture was extracted with chloroform
- washThe organic layer was washed with saturated brine
- customthe solvent was evaporated
Sources & evidence
- ORD record
- ord-8ac8ff68f094495dafa16ab62df9fcd3
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08354401B2
Reaction notes
Loading…