Triethylamine → (4RS,5SR)-4-[3-(1,1-difluoroethyl)benzyl]-5-(4-fluorophenyl)-1,3-oxazolidin-2-one

HRID 1610725노트

반응식

HRID 1610725 반응식
[F:1][C:2]([C:5]1[CH:6]=[C:7]([CH:22]=[CH:23][CH:24]=1)[CH2:8][CH:9]([CH:13]([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)[OH:14])C(O)=O)([F:4])[CH3:3].C([N:27]([CH2:30]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:39])C=CC=CC=1>O1CCCC1>[F:4][C:2]([C:5]1[CH:6]=[C:7]([CH:22]=[CH:23][CH:24]=1)[CH2:8][CH:9]1[CH:13]([C:15]2[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=2)[O:14][C:30](=[O:39])[NH:27]1)([F:1])[CH3:3]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 22261533(2RS,3RS)-2-[3-(1,1-difluoroethyl)benzyl]-3-(4-fluorophenyl)-3-hydroxypropionic acid

생성물 1

HCID 22261676(4RS,5SR)-4-[3-(1,1-difluoroethyl)benzyl]-5-(4-fluorophenyl)-1,3-oxazolidin-2-one수율 95%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (2RS,3RS)-2-[3-(1,1-difluoroethyl)benzyl]-3-(4-fluorophenyl)-3-hydroxypropionic acid (4.22 g, 13.6 mmol) in tetrahydrofuran (130 ml) were added triethylamine (2.85 ml, 20.4 mmol) and diphenylphosphoryl azide (3.23 ml, 14.96 mmol), and the mixture was heated under reflux for 5 hrs. The solvent was evaporated, and the residue was diluted with ethyl acetate, washed with water, saturated aqueous sodium hydrogen carbonate and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was recrystallized from hexane-ethyl acetate to give [4RS,5SR]-4-(3-[1,1-difluoroethyl)benzyl]-5-(4-fluorophenyl)-1,3-oxazolidin-2-one (3.99 g, 95%) as colorless crystals.

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hrs
  3. customThe solvent was evaporated
  4. additionthe residue was diluted with ethyl acetate
  5. washwashed with water, saturated aqueous sodium hydrogen carbonate and saturated brine
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was recrystallized from hexane-ethyl acetate

출처 및 근거

ORD 기록
ord-5b198d0e8b554405ade0dfcbc4c245e1
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06982348B2

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