N,N'-Dimethylethylenediamine → (R)-4-(4-isopropyl-2-oxooxazolidin-3-yl)benzoic acid

HRID 1803958Notes

Reaction equation

HRID 1803958 reaction equation
I[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8]CC)=[O:7])=[CH:4][CH:3]=1.[CH:13]([C@@H:16]1[CH2:20][O:19][C:18](=[O:21])[NH:17]1)([CH3:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+].CNCCNC>[Cu]I.O.C1(C)C=CC=CC=1>[CH:13]([C@@H:16]1[CH2:20][O:19][C:18](=[O:21])[N:17]1[C:2]1[CH:3]=[CH:4][C:5]([C:6]([OH:8])=[O:7])=[CH:11][CH:12]=1)([CH3:15])[CH3:14]

Participants

8

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 142891Ethyl 4-iodobenzoateHCID 641505(4R)-4-(Propan-2-yl)-1,3-oxazolidin-2-one

Product 1

HCID 58484694(R)-4-(4-isopropyl-2-oxooxazolidin-3-yl)benzoic acid

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a mixture of ethyl 4-iodobenzoate (5.8 mL), (R)-4-isopropyloxazolidin-2-one (5 g), potassium carbonate (15 g) and copper (I) iodide (1.3 g) were added toluene (35 mL) and N,N′-dimethylethylenediamine (1.5 mL), and the mixture was refluxed for 8 hr. After cooling, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated. The residue was dissolved in methanol (35 mL) and 1,4-dioxane (35 mL), 1N aqueous sodium hydroxide solution (70 mL) was added, and the mixture was stirred at room temperature overnight. 1N hydrochloric acid (70 mL) was added, and the mixture was filtered to give the title compound (9 g).

Workup

  1. temperaturethe mixture was refluxed for 8 hr
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. customthe solvent was evaporated
  6. dissolutionThe residue was dissolved in methanol (35 mL)
  7. addition1,4-dioxane (35 mL), 1N aqueous sodium hydroxide solution (70 mL) was added
  8. addition1N hydrochloric acid (70 mL) was added
  9. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-f5398e1ee5cf435aa37bb8416d37a96d
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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