Sodium hydride → 5-(2-Hydroxy-4-phenyl-2-trifluoromethyl-pentylamino)-phthalide

HRID 1698837ノート

反応式

HRID 1698837 の反応式
C([NH:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:10](=[O:11])[O:9][CH2:8]2)(=O)C.[H-].[Na+].[OH:17][C:18]([C:40]([F:43])([F:42])[F:41])([CH2:31][CH:32]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH3:33])[CH2:19]OS(C1C=CC(C)=CC=1)(=O)=O>CN(C)C=O>[OH:17][C:18]([C:40]([F:41])([F:42])[F:43])([CH2:31][CH:32]([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[CH3:33])[CH2:19][NH:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:10](=[O:11])[O:9][CH2:8]2

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 5909685-Acetamido-phthalideHCID 185511734-Toluenesulfonic acid-(2-hydroxy-4-phenyl-2-trifluoromethyl-pentyl)-ester

生成物 1

HCID 98427925-(2-Hydroxy-4-phenyl-2-trifluoromethyl-pentylamino)-phthalide収率 35.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

760 mg of 5-acetamido-phthalide in 20 ml of dimethylformamide is mixed at 0° C. with 144 mg of sodium hydride (80% in mineral oil), and, after 20 minutes, with 800 mg of 4-toluenesulfonic acid-(2-hydroxy-4-phenyl-2-trifluoromethyl-pentyl)-ester. After 16 hours at 60° C., the solvent is concentrated by evaporation in a vacuum, the residue is dissolved in ethyl acetate, washed with water, dried (Na2SO4) and concentrated by evaporation. After chromatography on silica gel with cyclohexane/ethyl acetate (2:1), 266 mg of 5-(2-hydroxy-4-phenyl-2-trifluoromethyl-pentylamino)-phthalide, melting point 110° C., is obtained.

後処理

  1. waitAfter 16 hours at 60° C.
  2. concentrationthe solvent is concentrated by evaporation in a vacuum
  3. dissolutionthe residue is dissolved in ethyl acetate
  4. washwashed with water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated by evaporation

出典と根拠

ORDレコード
ord-455feac1311841b88d48f9af2b15f3a2
出典データセット
uspto-grants-2002_02
特許番号
US06344454B1

反応ノート

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