Hydrogen Peroxide → HCID 86591289、化合物

HRID 1825847ノート

反応式

HRID 1825847 の反応式
[CH3:1][CH2:2][C@@H:3]1[S:8][C:7]2([CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)[NH:6][C:4]1=[O:5].FC(F)(F)C(O)=[O:18].OO>O>[CH2:2]([CH:3]1[C:4](=[O:5])[NH:6][C:7]2([CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)[S@:8]1=[O:18])[CH3:1]

参加物

5

反応物 3

HCID 784Hydrogen PeroxideHCID 6422Trifluoroacetic acidHCID 10013505Ngx-267

生成物 1

HCID 86591289HCID 86591289、化合物

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A solution of AF267B (1.72 gr, 0.008 mol) in water (2.5 ml) was cooled (ice-water bath) and trifluoroacetic acid (3.5 ml) was added. To the cold stirred obtained mixture was added hydrogen peroxide (30%, 0.57 ml, 0.008 mol), the cooling bath was removed and the reaction mixture was stirred at room temperature over night. Sodium sulfite was added and the pH of the solution was adjusted to 9 with a saturated solution of sodium carbonate. The aqueous phase was extracted with dichloromethan (2×100 ml) and then with ethyl acetate (1×50 ml). The organic extracts were combined, dried (MgSO4) and the solvent was evaporated. Flash chromatography (silica-gel 60, 230–400 mesh, Merck 1.09385, elution with methanol/chloroform/ammonium hydroxide 10:89:1 v/v) gave AF300. 1H NMR (CDCl3) δ 1.19 (t, j=7.3 Hz, 3H, CH3), 1.85–2.0 (m, 5H), 2.17 (m, 1H), 2.27 (m, 1H), 2.34 (s, 3H, NCH3), 2.26 (m, 2H), 3,30 (dd, j=3.56, 11.13 Hz, CH3CH2CH), 6.37 (br NH) ppm; MS (EI) m/e 230 (M+).

後処理

  1. additionwas added
  2. customobtained mixture
  3. customthe cooling bath was removed
  4. stirringthe reaction mixture was stirred at room temperature over night
  5. additionSodium sulfite was added
  6. extractionThe aqueous phase was extracted with dichloromethan (2×100 ml)
  7. dry with materialdried (MgSO4)
  8. customthe solvent was evaporated
  9. washFlash chromatography (silica-gel 60, 230–400 mesh, Merck 1.09385, elution with methanol/chloroform/ammonium hydroxide 10:89:1 v/v)
  10. customgave AF300

出典と根拠

ORDレコード
ord-862609ab66164c7ea0a898519dced558
出典データセット
uspto-grants-2006_05
特許番号
US07049321B2

反応ノート

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