4-Methyl-5-phenyl-2-oxazolidinone, (4S,5R)- → (4S,5R)-3-(2-Bromo-5-trifluoromethyl-benzyl)-4-methyl-5-phenyl-oxazolidin-2-one

HRID 456204

반응식

HRID 456204 반응식
[CH3:1][C@H:2]1[C@@H:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:5][C:4](=[O:13])[NH:3]1.C([Li])CCC.[Br:19][C:20]1[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][C:21]=1[CH2:22]Br>>[Br:19][C:20]1[CH:27]=[CH:26][C:25]([C:28]([F:29])([F:30])[F:31])=[CH:24][C:21]=1[CH2:22][N:3]1[C@@H:2]([CH3:1])[C@@H:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:5][C:4]1=[O:13]

참가 물질

4

반응물 3

HCID 8531614-Methyl-5-phenyl-2-oxazolidinone, (4S,5R)-HCID 27562491-Bromo-2-(bromomethyl)-4-(trifluoromethyl)benzeneHCID 178418339Butyllithium

생성물 1

HCID 66890163(4S,5R)-3-(2-Bromo-5-trifluoromethyl-benzyl)-4-methyl-5-phenyl-oxazolidin-2-one

반응 조건

온도
-78 °C

실험 절차

To (4S,5R)-(−)-4-methyl-5-phenyl-2-oxazolidinone (0.386 g, 2.13 mmol) in THY (7 mL) at −78° C. under N2 was added n-butyllithium (2.5M in hexanes; 0.94 mL, 2.35 mmol), and the mixture was stirred at −78° C. for 30 minutes. 2-Bromo-5-(trifluoromethyl)benzyl bromide (0.678 g, 2.13 mmol) was added, and the reaction was warmed to room temperature and stirred overnight. Once no starting material was seen by analytical LCMS, the mixture was transferred to a separatory funnel and partitioned between EtOAc and H2O. The organic layer was separated and washed with brine, dried over MgSO4, filtered, and concentrated to give the title compound.

후처리

  1. temperaturethe reaction was warmed to room temperature
  2. stirringstirred overnight
  3. customthe mixture was transferred to a separatory funnel
  4. custompartitioned between EtOAc and H2O
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-0dcd10a379fe4d3988482eab28883d73
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497381B2

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