Cesium carbonate → HCID 60030589, 화합물

HRID 497569노트

반응식

HRID 497569 반응식
C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:8][CH2:9][CH2:10][C:11]([F:14])([F:13])[F:12].[C:15]([O:19][C:20]([NH:22][C@@H:23]([CH2:28][C:29]1[N:30]=[CH:31][NH:32][CH:33]=1)[C:24]([O:26][CH3:27])=[O:25])=[O:21])([CH3:18])([CH3:17])[CH3:16]>CN(C)C=O>[C:15]([O:19][C:20]([NH:22][C@@H:23]([CH2:28][C:29]1[N:30]=[CH:31][N:32]([CH2:8][CH2:9][CH2:10][C:11]([F:14])([F:13])[F:12])[CH:33]=1)[C:24]([O:26][CH3:27])=[O:25])=[O:21])([CH3:18])([CH3:16])[CH3:17]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 5210064-Bromo-1,1,1-trifluorobutaneHCID 178501431HCID 178501431, 화합물

생성물 1

HCID 60030589HCID 60030589, 화합물수율 55%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
70 °C

실험 절차

Cesium carbonate (1.95 g, 6 mmol) and 1-bromo-4,4,4-trifluorobutane (954 mg, 5 mmol) were added to a solution of methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-(1H-imidazol-4-yl)propanoate (1.08 g, 4 mmol) in N,N-dimethylformamide (5 ml), and the reaction stirred at 70° C. for 3 hours. The cooled mixture was concentrated under reduced pressure and the residue partitioned between ethyl acetate (150 ml) and water (50 ml). The layers were separated, the organic phase dried (MgSO4), filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel using an elution gradient of cyclohexane:ethyl acetate (100:0 to 0:100) to afford the title compound as an oil, 840 mg, 55% yield.

후처리

  1. concentrationThe cooled mixture was concentrated under reduced pressure
  2. customthe residue partitioned between ethyl acetate (150 ml) and water (50 ml)
  3. customThe layers were separated
  4. dry with materialthe organic phase dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography on silica gel using an elution gradient of cyclohexane:ethyl acetate (100:0 to 0:100)

출처 및 근거

ORD 기록
ord-ff96d8c114f9406698548ef633072fec
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06949577B2

반응 노트

불러오는 중…