Reaction #2329057

Reaction equation

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

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

hydrogen

magnesium sulfate

→

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

Solvents

tetrahydrofuran

ammonia

Conditions

Workup

1. 1
   Filtrationthe reaction solution was filtered
2. 2
   ConcentrationThe filtrate was concentrated
3. 3
   Otherseparated by HPLC (Knauer Eurospher-100-10-C18, water (0.1% trifluoroacetic acid)/acetonitrile (0.1% trifluoro-acetic acid)=80/20→10/90)
4. 4
   OtherThis gave the product of molecular weight 435.48 (C25H23F2N3O2)

Procedure

100 mg of 4-{1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin-2-yl}-N-hydroxybenzamidine (3) were dissolved in 100 ml of tetrahydrofuran and, with 2 ml of conc. ammonia, hydrogenated over Raney nickel at a hydrogen pressure of 75 bar and 25° C. for 30 hours. After addition of magnesium sulfate, the reaction solution was filtered. The filtrate was concentrated and separated by HPLC (Knauer Eurospher-100-10-C18, water (0.1% trifluoroacetic acid)/acetonitrile (0.1% trifluoro-acetic acid)=80/20→10/90). This gave the product of molecular weight 435.48 (C25H23F2N3O2); MS (ESI): 436.18 (M+H+).

Source