Reaktion #1934019

Reaktionsgleichung

N-(5-benzyloxy-6-formyl-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamide

sulfamic acid

sodium chlorite

water

→

6-(benzene sulfonyl amino-methyl)-3-benzyloxy-4-oxo-4H-pyran-2-carboxylic acid

Ausbeute 87.8%

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter completion of the reaction
2. 2
   Sonstigethe solvent and the volatile substances were removed
3. 3
   Extraktionextracted with dichloromethane
4. 4
   WaschenThe combined organic layer was washed with saturated ammonium chloride solution, water
5. 5
   Trocknenbrine, dried over Na2SO4
6. 6
   Einengenconcentrated under reduced pressure

Vorschrift

To a stirred solution of N-(5-benzyloxy-6-formyl-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamide (11-01) (700.0 mg, 1.75 mmol) in acetone (10 mL) and water (15 mL) were added sulfamic acid (240.45 mg, 2.45 mmol) and sodium chlorite (166.6 mg, 1.84 mmol) and the reaction mixture was allowed to stir for 16 h at room temperature. After completion of the reaction, the solvent and the volatile substances were removed and extracted with dichloromethane. The combined organic layer was washed with saturated ammonium chloride solution, water and then brine, dried over Na2SO4 and concentrated under reduced pressure to get 6-(benzene sulfonyl amino-methyl)-3-benzyloxy-4-oxo-4H-pyran-2-carboxylic acid (12-01) (640.0 mg, 87.82%) as a white solid.

Quelle