Hydrogen Peroxide → HCID 86591289, compound

HRID 1825847Notes

Reaction equation

HRID 1825847 reaction equation
[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]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 6422Trifluoroacetic acidHCID 10013505AF 267B

Product 1

HCID 86591289HCID 86591289, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-862609ab66164c7ea0a898519dced558
Source dataset
uspto-grants-2006_05
Patent number
US07049321B2

Reaction notes

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