Reaction #2329059

Reaction equation

hydroxylammonium hydrochloride

4-[3-[3-(4-fluorophenyl)-3-hydroxypropyl]-2-(4-fluorophenyl)-4-oxoazetidin-1-yl]benzonitrile

4-[3-[-(4-Fluorophenyl)-3-hydroxypropyl]-2-(4-fluorophenyl)-4-oxoazetidin-1-yl]benzonitrile

triethylamine

→

4-{2-(4-Fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin-1-yl}-N-hydroxybenzamidine

Solvents

isopropanol

Conditions

Workup

1. 1
   ExtractionThe reaction solution was extracted twice with ethyl acetate/water
2. 2
   DryingThe organic phases were dried over magnesium sulfate
3. 3
   Concentrationconcentrated
4. 4
   OtherThis gave the product of molecular weight 451.48 (C25H23F2N3O3)

Procedure

279 mg of hydroxylammonium hydrochloride were added to a solution of 280 mg of 4-[3-[3-(4-fluorophenyl)-3-hydroxypropyl]-2-(4-fluorophenyl)-4-oxoazetidin-1-yl]benzonitrile (11) and 0.65 ml of triethylamine in 15 ml of isopropanol. The mixture was stirred at room temperature for 12 h. The reaction solution was extracted twice with ethyl acetate/water. The organic phases were dried over magnesium sulfate and concentrated. This gave the product of molecular weight 451.48 (C25H23F2N3O3); MS (ESI): 452.10 (M+H+).

Source