Ammonium Chloride → (4S)-4-Phenyl-3-(3-phenylprop-2-enoyl)-1,3-oxazolidin-2-one

HRID 53351

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HRID 53351 반응식
[C:1]1([C@H:7]2[CH2:11][O:10][C:9](=[O:12])[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[C:18](Cl)(=[O:27])/[CH:19]=[CH:20]/[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[NH4+].[Cl-]>C1COCC1>[C:18]([N:8]1[C@@H:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:11][O:10][C:9]1=[O:12])(=[O:27])/[CH:19]=[CH:20]/[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 7304242-Oxazolidinone, 4-phenyl-, (4S)-HCID 5354261Cinnamoyl ChlorideHCID 178418339Butyllithium

생성물 1

HCID 679769(4S)-4-Phenyl-3-(3-phenylprop-2-enoyl)-1,3-oxazolidin-2-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

(S)-(+)-4-Phenyl-2-oxazolidinone (4.77 g, 29.3 mmol, Aldrich) was dissolved in dry THF (100 mL), and the solution was cooled to -78° C. and flushed with N2. n-Butyllithium (2.5M in THF, 11.7 mL, 29.3 mmol) was introduced over 10 minutes. The compound from step 8a (in 30 mL of THF) was added over 10 minutes, and the mixture was stirred at -78° C. for half an hour. The mixture was stirred as it was allowed to warm to room temperature. Saturated aqueous NH4Cl solution was added, the mixture was stirred for 10 minutes and the THF was removed under reduced pressure. The residue was dissolved in ethyl acetate, and the solution was washed with water, 5% aqueous NaHCO3 and brine, then dried over Na2SO4. The solvent was removed to afford the title compound, which was recrystallized from ethyl acetate to give the title product (7.18 g). MS m/z 294 (M+H)+, 311 (M+NH4)+.

후처리

  1. customflushed with N2
  2. stirringThe mixture was stirred as it
  3. temperatureto warm to room temperature
  4. stirringthe mixture was stirred for 10 minutes
  5. customthe THF was removed under reduced pressure
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. washthe solution was washed with water, 5% aqueous NaHCO3 and brine
  8. dry with materialdried over Na2SO4
  9. customThe solvent was removed

출처 및 근거

ORD 기록
ord-0811c857f5db4ea5a7e911d4b6395759
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05618949

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