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

HRID 1749469ノート

反応式

HRID 1749469 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-21da591480c0415f921cd0e14e81cbc6
出典データセット
uspto-grants-2015_10
特許番号
US09156798B2

反応ノート

読み込み中…