Boron tribromide → N-(2,6-dichlorobenzoyl)-4-(6-methoxy-2-hydoxyphenyl)-L-phenylalanine ethyl ester

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Reaction Conditions

Reaction Steps

N-(2,6-Dichlorobenzoyl)-4-(2,6-dimethoxyphenyl)-L-phenylalanine, ethyl ester (0.16 g, prepared in a fashion similar to that of the methyl ester described in Example 8) was dissolved in anhydrous CH2Cl2 (8 mL). The solution was cooled to −78° C. and BBr3 (0.56 mL, 1 M solution in CH2Cl2) was added. The mixture was allowed to warm to 0° C., and stirred at that temperature for 2 h. The mixture was subsequently warmed to room temperature and quenched with satd. NaHCO3 (5 mL). The mixture was stirred for 1 h, and diluted with CH2Cl2. The organic phase was dried (MgSO4) and concentrated. The residue was purified by flash column chromatography (silica gel; eluent: EtOAc/hexanes 1:2) to give 40 mg of N-(2,6-dichlorobenzoyl)-4-(2-hydroxy-6-methoxyphenyl)-L-phenylalanine ethyl ester ESMS: m/z 488 (MH+).

Provenance & Evidence