Cesium carbonate → HCID 60030589、化合物

HRID 497569ノート

反応式

HRID 497569 の反応式
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]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 5210064-Bromo-1,1,1-trifluorobutaneHCID 178501431HCID 178501431、化合物

生成物 1

HCID 60030589HCID 60030589、化合物収率 55%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-ff96d8c114f9406698548ef633072fec
出典データセット
uspto-grants-2005_09
特許番号
US06949577B2

反応ノート

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