phenyl N-benzyloxycarbamate → 1-(N-benzyloxycarbamoyl)-3-(3,5-di-tert-butyl-4-hydroxybenzylidene)pyrrolidin-2-one

HRID 1109358ノート

反応式

HRID 1109358 の反応式
[C:1]([C:5]1[CH:6]=[C:7]([CH:15]=[C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:17]=1[OH:18])[CH:8]=[C:9]1[CH2:13][CH2:12][NH:11][C:10]1=[O:14])([CH3:4])([CH3:3])[CH3:2].[CH2:23]([O:30][NH:31][C:32](=O)[O:33]C1C=CC=CC=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>N1C=CC=CC=1>[CH2:23]([O:30][NH:31][C:32]([N:11]1[CH2:12][CH2:13][C:9](=[CH:8][C:7]2[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:17]([OH:18])=[C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:15]=2)[C:10]1=[O:14])=[O:33])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

参加物

4

反応物 2

HCID 11644415phenyl N-benzyloxycarbamateHCID 538962973-(3,5-Di-tert-butyl-4-hydroxybenzylidene)-2-pyrrolidone

生成物 1

HCID 538058911-(N-benzyloxycarbamoyl)-3-(3,5-di-tert-butyl-4-hydroxybenzylidene)pyrrolidin-2-one収率 61%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

3-(3,5-Di-tert-butyl-4-hydroxybenzylidene)pyrrolidin-2-one (600 mg, 2 mmole) and phenyl N-benzyloxycarbamate (490 mg, 2.01 mmole) were dissolved into 8 ml of pyridine and the solution was heated under reflux for 12 hours. The reaction mixture was evaporated and the obtained residue was dissolved into ethyl acetate, which was washed with an aqueous solution of 0.1N hydrochloric acid, water, and saturated brine, dried over magnesium sulfate, and evaporated. The obtained residue was separated by using silica gel chromatography (toluene:ethyl acetate=10:1) and recrystallized from dichloromethane/n-hexane, whereby 550 mg of the objective compound (Ia-10) was obtained in 61% yield.

後処理

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 12 hours
  3. customThe reaction mixture was evaporated
  4. dissolutionthe obtained residue was dissolved into ethyl acetate, which
  5. washwas washed with an aqueous solution of 0.1N hydrochloric acid, water, and saturated brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe obtained residue was separated
  9. customrecrystallized from dichloromethane/n-hexane

出典と根拠

ORDレコード
ord-790f1b99c63a4c5ab67af77981c64cf4
出典データセット
uspto-grants-1994_06
特許番号
US05319099

反応ノート

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