m-Chloroperbenzoic acid → 3-(2-((tert-Butoxycarbonyl)amino)ethyl)-5-chloropyridine 1-oxide

HRID 1749469Notes

Reaction equation

HRID 1749469 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:5]=[N:6][CH:7]=1.ClC1C=CC=C(C(OO)=[O:26])C=1>C(Cl)Cl>[C:13]([O:12][C:11]([NH:10][CH2:9][CH2:8][C:4]1[CH:5]=[N+:6]([O-:26])[CH:7]=[C:2]([Cl:1])[CH:3]=1)=[O:17])([CH3:14])([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 131733585tert-butyl(2-(5-Chloropyridin-3-yl)ethyl)carbamate

Product 1

HCID 1181621543-(2-((tert-Butoxycarbonyl)amino)ethyl)-5-chloropyridine 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (2-(5-chloropyridin-3-yl)ethyl)carbamate (93 mg, 0.36 mmol) in DCM (4 mL) was added 3-chloroperbenzoic acid (85%, 94.8 mg, 0.54 mmol) at 0° C. The resulting reaction mixture was stirred at room temperature for 1.5 h. The reaction was quenched with aqueous solution of sodium thiosulfate and extracted with DCM. The combined organic layers were washed with aqueous solution of potassium carbonate and brine, dried over sodium sulfate and concentrate to give a crude product, which was used directly in the next step without further purification (90 mg, crude). MS (ESI) m/z 273.1 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. customThe reaction was quenched with aqueous solution of sodium thiosulfate
  3. extractionextracted with DCM
  4. washThe combined organic layers were washed with aqueous solution of potassium carbonate and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-21da591480c0415f921cd0e14e81cbc6
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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