Reacción #52920

Ecuación de reacción

BBr3

N-(2,6-dichlorobenzoyl)-4-(2-methoxyphenyl)-L-phenylalanine methyl ester

→

N-(2,6-dichlorobenzoyl)-4-(2-hydroxyphenyl)-L-phenylalanine methyl ester

Rendimiento 50.4%

Disolventes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe mixture was stirred for 3 h
2. 2
   Otroquenched with EtOH
3. 3
   OtroThe solvent was removed
4. 4
   LavadoThe solution was washed with satd
5. 5
   Secadodried (MgSO4)
6. 6
   Otroevaporated
7. 7
   OtroThe residue was purified by flash column chromatography (silica gel; eluent: hexanes/EtOAc 2:1)

Procedimiento

BBr3 (1 mL, 1M in CH2Cl2) was added to a CH2Cl2 (10 mL) solution of N-(2,6-dichlorobenzoyl)-4-(2-methoxyphenyl)-L-phenylalanine methyl ester (0.215 g) at 0° C. with stirring and the solution was slowly warmed to room temperature. The mixture was stirred for 3 h and quenched with EtOH. The solvent was removed and the residue was taken up in EtOAc. The solution was washed with satd. NaHCO3 followed by brine, dried (MgSO4) and evaporated. The residue was purified by flash column chromatography (silica gel; eluent: hexanes/EtOAc 2:1) to yield 0.105 g of N-(2,6-dichlorobenzoyl)-4-(2-hydroxyphenyl)-L-phenylalanine methyl ester. ESMS: m/z 444 (MH+).

Fuente