Acetic Acid → 3-(4-Amino-2-fluorobenzyl)-1,3-oxazolidin-2-one

HRID 1094023노트

반응식

HRID 1094023 반응식
[F:1][C:2]1[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[CH:11][C:3]=1[CH2:4][N:5]1[CH2:9][CH2:8][O:7][C:6]1=[O:10].C(O)(=O)C.[OH-].[Na+]>C(O)C.[Fe]>[NH2:15][C:13]1[CH:12]=[CH:11][C:3]([CH2:4][N:5]2[CH2:9][CH2:8][O:7][C:6]2=[O:10])=[C:2]([F:1])[CH:14]=1

참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 666368043-(2-Fluoro-4-nitrobenzyl)-1,3-oxazolidin-2-one

생성물 1

HCID 647676883-(4-Amino-2-fluorobenzyl)-1,3-oxazolidin-2-one

시약·촉매·용매 2

HCID 23925Iron촉매HCID 702Ethanol용매

실험 절차

To a solution of the compound obtained in Step B (10.37 mmoles) in ethanol (25 ml) there are added 122 microlitres of acetic acid. The solution is heated at reflux and stirred for 10 minutes. Powdered iron (2.08 g) and 75 mg of FeCl3.6H2O are added. After stirring for 2 hours at reflux, the mixture is brought to ambient temperature and then concentrated to dryness. 50 ml of water are added to the residue obtained, and the pH is made alkaline using sodium hydroxide. The solution is extracted 4 times with AcOEt. The organic phases are combined and washed with saturated aqueous NaCl solution and then dried with MgSO4. After filtration, the organic phase is evaporated to dryness to yield the title product, which is used directly in the next Step.

후처리

  1. temperatureThe solution is heated
  2. temperatureat reflux
  3. stirringAfter stirring for 2 hours
  4. temperatureat reflux
  5. customis brought to ambient temperature
  6. concentrationconcentrated to dryness
  7. addition50 ml of water are added to the residue
  8. customobtained
  9. extractionThe solution is extracted 4 times with AcOEt
  10. washwashed with saturated aqueous NaCl solution
  11. dry with materialdried with MgSO4
  12. filtrationAfter filtration
  13. customthe organic phase is evaporated to dryness

출처 및 근거

ORD 기록
ord-a68832dc6d3c45c49ed1d8b579c78af5
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08133889B2

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