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

HRID 6189Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 6189
[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]

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-15f297c6101148ec9fd927b43a15d2da
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05246948

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