m-Chloroperbenzoic acid → 4-[3-(t-Butoxycarbonylamino)propylsulfinyl]pyridine

HRID 864028노트

반응식

HRID 864028 반응식
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][S:12][C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:27])C=1>C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][S:12]([C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)=[O:27])=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

4

반응물 2

HCID 70297m-Chloroperbenzoic acidHCID 145388644-(3-Tert-butoxycarbonylaminopropylthio)pyridine

생성물 1

HCID 190791514-[3-(t-Butoxycarbonylamino)propylsulfinyl]pyridine수율 79%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 4.03 g (15.0 mmol) of 4-[3-(t-butoxycarbonylamino)propylthio]pyridine in 100 ml of methylene chloride, 3.05 g (15.0 mmol) of m-chloroperbenzoic acid was added with stirring under ice-cooling, and the mixture was stirred at the same temperature for 1 hour. The reaction mixture was washed two times with saturated aqueous sodium bicarbonate and dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by column chromatography (eluent:ethyl acetate/ethanol=10:1) to give 3.37 g of the desired compound (78.9% yield, colorless crystals).

후처리

  1. temperaturecooling
  2. stirringthe mixture was stirred at the same temperature for 1 hour
  3. washThe reaction mixture was washed two times with saturated aqueous sodium bicarbonate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was purified by column chromatography (eluent:ethyl acetate/ethanol=10:1)

출처 및 근거

ORD 기록
ord-0688c165795a438faa2d8d80aae4f952
출처 데이터셋
uspto-grants-1996_10
특허 번호
US05561147

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