Reaktion #52920

Reaktionsgleichung

BBr3

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

→

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

Ausbeute 50.4%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe mixture was stirred for 3 h
2. 2
   Sonstigequenched with EtOH
3. 3
   SonstigeThe solvent was removed
4. 4
   WaschenThe solution was washed with satd
5. 5
   Trocknendried (MgSO4)
6. 6
   Sonstigeevaporated
7. 7
   SonstigeThe residue was purified by flash column chromatography (silica gel; eluent: hexanes/EtOAc 2:1)

Vorschrift

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+).

Quelle