반응 #52920

반응 방정식

BBr3

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

→

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

수율 50.4%

용매

CH2Cl2

반응 조건

후처리

1. 1
   workup.STIRRINGThe mixture was stirred for 3 h
2. 2
   기타quenched with EtOH
3. 3
   기타The solvent was removed
4. 4
   세척The solution was washed with satd
5. 5
   건조dried (MgSO4)
6. 6
   기타evaporated
7. 7
   기타The residue was purified by flash column chromatography (silica gel; eluent: hexanes/EtOAc 2:1)

실험 절차

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+).

출처