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

HRID 1109292노트

반응식

HRID 1109292 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e0e1b7afab6d407aab8c805ffb493e9d
출처 데이터셋
uspto-grants-1994_06
특허 번호
US05319100

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