3,5-Dichloro-1-fluoropyridinium triflate → N-(2,6-dichlorobenzoyl)-4-(2,6-dimethoxy-3-fluorophenyl)-L-phenylalanine methyl ester

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Reaction Steps

N-(2,6-Dichlorobenzoyl)-4-(2,6-dimethoxyphenyl)-L-phenylalanine methyl ester (232 mg) was dissolved in anhydrous MeCN (10 mL) under N2 and 3,5-dichloro-1-fluoropyridinium triflate (85%, 353 mg) was added and the mixture was refluxed for 1 day. More 3,5-dichloro-1-fluoropyridinium triflate (175 mg) was added and the mixture was refluxed for another day. The mixture was then concentrated, and the residue was taken up with water and extracted with CH2Cl2. The extract Was washed with sat. NaHCO3, water, dried (MgSO4), filtered and evaporated. The residue was purified by preparative TLC (silica gel; eluent: hexane/AcOEt 5:1 to 2:1) to give N-(2,6-dichlorobenzoyl)-4-(2,6-dimethoxy-3-fluorophenyl)-L-phenylalanine methyl ester (109 mg) and N-(2,6-dichlorobenzoyl)-4-(2,6-dimethoxy-3,5-difluorophenyl)-L-phenylalanine methyl ester (37 mg).

Provenance & Evidence