Water → 1,1-Dimethylethyl [(4r)-4-(5-chloro-2-cyano-4-fluorophenoxy)-4-(1-methyl-1h-imidazol-2-yl)butyl]-carbamate

HRID 352132ノート

反応式

HRID 352132 の反応式
[CH3:1][C:2]([O:5][C:6](=[O:19])[NH:7][CH2:8][CH2:9][CH2:10][C@@H:11]([OH:18])[C:12]1[N:13]([CH3:17])[CH:14]=[CH:15][N:16]=1)([CH3:4])[CH3:3].[H-].[Na+].[Cl:22][C:23]1[C:30]([F:31])=[CH:29][C:26]([C:27]#[N:28])=[C:25](F)[CH:24]=1.O>CN(C)C=O>[Cl:22][C:23]1[C:30]([F:31])=[CH:29][C:26]([C:27]#[N:28])=[C:25]([CH:24]=1)[O:18][C@@H:11]([C:12]1[N:13]([CH3:17])[CH:14]=[CH:15][N:16]=1)[CH2:10][CH2:9][CH2:8][NH:7][C:6](=[O:19])[O:5][C:2]([CH3:1])([CH3:3])[CH3:4]

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 112753024-Chloro-2,5-difluorobenzonitrileHCID 131724444[(4R)-4-Hydroxy-4-(1-methyl-1H-imidazol-2-yl)butyl]carbamic acid 1,1-dimethylethyl ester

生成物 1

HCID 914130451,1-Dimethylethyl [(4r)-4-(5-chloro-2-cyano-4-fluorophenoxy)-4-(1-methyl-1h-imidazol-2-yl)butyl]-carbamate収率 89.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

The product of step (b) (0.24 g, 0.9 mmol) was dissolved in dry dimethylformamide (20 ml), sodium hydride (60% dispersion in oil, 0.04 g, 0.95 mmol) was added in one portion and the mixture stirred at room temperature for 0.5 h. 4-Chloro-2,5-difluorobenzonitrile (0.16 g, 0.9 mmol), as a solution in dry dimethylformamide (5 ml), was added dropwise and the reaction stirred for 18hat room temperature. Water (25 ml) was added and the reaction mixture extracted with ethyl acetate (3×60 ml). The combined organic extracts were washed with water (2×20 ml), dried (magnesium sulphate) and evaporated. The residue was eluted down a flash chromatography column using hexane:ethyl acetate (1:3) as eluent to give the sub-title compound as a white crystalline solid (0.34 g, 88%).

後処理

  1. stirringthe reaction stirred for 18hat room temperature
  2. extractionthe reaction mixture extracted with ethyl acetate (3×60 ml)
  3. washThe combined organic extracts were washed with water (2×20 ml)
  4. dry with materialdried (magnesium sulphate)
  5. customevaporated
  6. washThe residue was eluted down a flash chromatography column

出典と根拠

ORDレコード
ord-45c373d6c6844181bfd1b0354ab65a95
出典データセット
uspto-grants-2004_06
特許番号
US06743939B2

反応ノート

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