Potassium Permanganate → N-(2,6-dichlorobenzoyl)-4-(2-carboxyphenyl)-L-phenylalanine methyl ester

Participants

Reaction Conditions

Reaction Steps

N-(2,6-Dichlorobenzoyl)-4-(2-formylphenyl)-L-phenylalanine methyl ester (104 mg) was dissolved in acetone (700 μL) by warming up to about 40° C. A warm (40° C.) solution of KMnO4 (61.2 mg) in a mixture of acetone (900 μL) and water (130 μL) was then added over a 1 h period and the resulting mixture was stirred at that temperature for an additional 2 h. The mixture was filtered through Celite and washed with acetone. The filtrate was taken up with water and acidified to approximately pH 2 with 1N HCl, and extracted with EtOAc. The combined extracts were dried (MgSO4) and evaporated. The residue was purified through a silica gel column using toluene then a gradient of toluene/EtOAc (20:1 to 3:1) as an eluent to give N-(2,6-dichlorobenzoyl)-4-(2-carboxyphenyl)-L-phenylalanine methyl ester (85.0 mg). ESMS: m/z 472 (MH+).

Provenance & Evidence