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

HRID 864028Notes

Reaction equation

HRID 864028 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-0688c165795a438faa2d8d80aae4f952
Source dataset
uspto-grants-1996_10
Patent number
US05561147

Reaction notes

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