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

HRID 1803958노트

반응식

HRID 1803958 반응식
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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 962Water용매HCID 1140Toluene용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f5398e1ee5cf435aa37bb8416d37a96d
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354401B2

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