Reaktion #310540

ord-82029858ee1c4b3dbc75f90598e80ee4

Reaktionsgleichung

O=C(O)CN(CCN(CC(=O)O)CC(=O)O)CC(=O)O
ethylenediamine tetraacetic acid
O=C1O[C@H]([C@@H](O)CO)C(O)=C1O
ascorbic acid
COc1cc(S(C)=O)ccc1-c1nc2ncccc2[nH]1
2-(2-methoxy-4-methylsulfinyl-phenyl)-1H-imidazo[4,5-b]pyridine
COc1cc(S(C)=O)ccc1-c1nc2ncc(O)cc2[nH]1
2-(2-Methoxy-4-methylsulfinyl-phenyl)-6-hydroxy-1H-imidazo[4,5-b]pyridine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeAfter 30 minutes the reaction mixture was evaporated in vacuo
  2. 2
    Sonstigethe residue was purified by chromatography on a polystyrene resin column (XAD-2 of Rohm & Haas) with water and methanol as eluants
  3. 3
    SonstigeAfter evaporation of the eluate the two compounds
  4. 4
    Sonstigewere separated by means of chromatography on silicagel [eluant: chloroform/methanol/ammonia water=85/15/2 (v/v)]

Vorschrift

7.2 gm of 2-(2-methoxy-4-methylsulfinyl-phenyl)-1H-imidazo[4,5-b]pyridine were dissolved in a mixture of a phosphate buffer of pH 7.2 and 120 ml of 3% hydrogen peroxide, and a solution of 9.3 gm of ethylenediamine tetraacetic acid, 4.4 gm of ascorbic acid, 3.8 gm of iron(II) sulfate in a phosphate buffer of pH 7.2 was added. After 30 minutes the reaction mixture was evaporated in vacuo, and the residue was purified by chromatography on a polystyrene resin column (XAD-2 of Rohm & Haas) with water and methanol as eluants. After evaporation of the eluate the two compounds were separated by means of chromatography on silicagel [eluant: chloroform/methanol/ammonia water=85/15/2 (v/v)]. 2-(2-Methoxy-4-methylsulfinyl-phenyl)-6-hydroxy-1H-imidazo[4,5-b]pyridine was obtained as yellow powder.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04353909uspto-grants-1982_10