반응 #52905

반응 방정식

2,6-Dimethoxybenzeneboronic acid

K2CO3

N-(tert-butoxycarbonyl)-O-(trifluoromethane-sulfonyl)-L-tyrosine methyl ester

→

N-(tert-butoxycarbonyl)-4-(2,6-dimethoxyphenyl)-L-phenylalanine methyl ester

수율 97.7%

용매

DME

water

water

EtOAc

반응 조건

후처리

1. 1
   건조The EtOAc layer was dried (MgSO4)
2. 2
   기타evaporated
3. 3
   기타The residue was purified by flash column chromatography (silica gel; eluent: EtOAc/hexane 1:2)

실험 절차

2,6-Dimethoxybenzeneboronic acid (0.5 g) was dissolved in DME (10 mL). To the solution was added K2CO3 (0.7 g), N-(tert-butoxycarbonyl)-O-(trifluoromethane-sulfonyl)-L-tyrosine methyl ester (0.4 g), Pd(Ph3P)4 (0.6 g) and water (0.2 mL). The resulting mixture was heated to 80° C. overnight. Subsequently EtOAc and water were added to the mixture. The EtOAc layer was dried (MgSO4) and evaporated. The residue was purified by flash column chromatography (silica gel; eluent: EtOAc/hexane 1:2) to give N-(tert-butoxycarbonyl)-4-(2,6-dimethoxyphenyl)-L-phenylalanine methyl ester (380 mg).

출처