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

HRID 1749469Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1749469
[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]

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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]+.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-21da591480c0415f921cd0e14e81cbc6
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156798B2

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