Phosphorus oxychloride → 4-(2-Benzyloxy-ethyl)-2-(4-bromo-2-fluoro-phenyl)-5-methyl-oxazole

HRID 1445763노트

반응식

HRID 1445763 반응식
[CH2:1]([O:8][CH2:9][CH2:10][CH:11]([NH:15][C:16](=[O:25])[C:17]1[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][C:18]=1[F:24])[C:12](=O)[CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O>CN(C)C=O>[CH2:1]([O:8][CH2:9][CH2:10][C:11]1[N:15]=[C:16]([C:17]2[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][C:18]=2[F:24])[O:25][C:12]=1[CH3:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 24813Phosphorus oxychlorideHCID 58951463N-[1-(2-Benzyloxy-ethyl)-2-oxo-propyl]-4-bromo-2-fluoro-benzamide2회

생성물 1

HCID 589514114-(2-Benzyloxy-ethyl)-2-(4-bromo-2-fluoro-phenyl)-5-methyl-oxazole

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirring solution of N-[1-(2-benzyloxy-ethyl)-2-oxo-propyl]-4-bromo-2-fluoro-benzamide (1.0 mmol) (See Intermediate 36) in dimethylformamide (0.25M), slowly add phosphorus oxychloride (3.0 mmol) and heat to 90° C. for 2.5 hours. After this time, remove the heat and carefully add water (same amount as DMF) and allow the reaction to cool to room temperature before extracting with ether. Wash organics with water and brine. Dry the organics with sodium sulfate, filter and concentrate in vacuo. Purify via radial chromatography eluting with ethyl acetate and hexane. MS (m/e) (79Br/81Br): 390.2/392.2 (M+1)

후처리

  1. customAfter this time, remove the
  2. temperatureheat
  3. customthe reaction
  4. extractionbefore extracting with ether
  5. dry with materialDry the organics with sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. customPurify via radial chromatography
  9. washeluting with ethyl acetate and hexane

출처 및 근거

ORD 기록
ord-65ef94116c9449c6bca22a5257c7de1b
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07666871B2

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