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Cesium carbonate → Diethyl 2,2'-((5-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)oxazol-2-yl)azanediyl)diacetate

HRID 68320
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인쇄 미리보기

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HRID 68320 반응식
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[OH:19][N:20]=[C:21]([C:23]1[O:27][C:26]([N:28]([CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[N:25][CH:24]=1)[CH3:22]>CN(C=O)C>[F:10][C:9]([F:12])([F:11])[C:6]1[CH:7]=[CH:8][C:3]([CH2:2][O:19][N:20]=[C:21]([C:23]2[O:27][C:26]([N:28]([CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[N:25][CH:24]=2)[CH3:22])=[CH:4][CH:5]=1
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참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 86699627Diethyl 2,2'-((5-(1-(hydroxyimino)ethyl)oxazol-2-yl)azanediyl)diacetate

생성물 1

HCID 86699628Diethyl 2,2'-((5-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)oxazol-2-yl)azanediyl)diacetate수율 75%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

To a solution of 1-(bromomethyl)-4-(trifluoromethyl)benzene (200 mg, 0.84 mmoles) in DMF (2 mL), cesium carbonate (408 mg, 1.26 mmoles) was added followed by addition of diethyl 2,2′-((5-(1-(hydroxyimino)ethyl)oxazol-2-yl)azanediyl)diacetate (262 mg, 0.84 mmoles) at 25° C. under nitrogen atmosphere and the reaction mixture was stirred at the same temperature for 18 h. The reaction mixture was poured into ice cold water and extracted with ethyl acetate. The combined ethyl acetate extract was washed with water & brine, dried over sodium sulphate and evaporated under reduced pressure. The crude product was purified by column chromatography (Eluent: 15% ethyl acetate in hexane) to yield 295 mg (75%) product as thick liquid.

후처리

  1. additionThe reaction mixture was poured into ice cold water
  2. extractionextracted with ethyl acetate
  3. extractionThe combined ethyl acetate extract
  4. washwas washed with water & brine
  5. dry with materialdried over sodium sulphate
  6. customevaporated under reduced pressure
  7. customThe crude product was purified by column chromatography (Eluent: 15% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-af5626932dec4aa0816055572b30561f
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08822414B2

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