反应详情

温度

80 °C

A mixture of 2,6-dimethoxy-4-(tert-butyl-diphenylsilyloxy)benzeneboronic acid (3 g), N-(2,6-dichlorobenzoyl)-4-bromo-L-phenylalanine ethyl ester (0.8 g), Pd(PPh3)4 (1 g) and K2CO3 (2.1 g) in DME/H2O (20 mL/0.5 mL) was heated at 80° C. for 6 hour under N2. The mixture was diluted with EtOAc and washed with water, dried and evaporated. The residue was dissolved in EtOAc and the solution was filtered through a silica gel column and evaporated. The residue was dissolved in THF, and TBAF (1.6 M in THF, 4 ml) was added. The mixture was stirred at room temperature for 1 hour, diluted with water and extracted with EtOAc. The extract was washed with water, dried and evaporated. The residue was purified by flash column chromatography (silica gel; eluent: EtOAc/hexane 1/2) to yield 0.5 g of N-(2,6-dichlorobenzoyl)-4-(2,6-dimethoxy-4-hydroxyphenyl)-L-phenylalanine ethyl ester. ESMS m/z: 490 (MH+).

1. washwashed with water
2. customdried
3. customevaporated
4. dissolutionThe residue was dissolved in EtOAc
5. filtrationthe solution was filtered through a silica gel column
6. customevaporated
7. dissolutionThe residue was dissolved in THF
8. additionTBAF (1.6 M in THF, 4 ml) was added
9. additiondiluted with water
10. extractionextracted with EtOAc
11. washThe extract was washed with water
12. customdried
13. customevaporated
14. customThe residue was purified by flash column chromatography (silica gel; eluent: EtOAc/hexane 1/2)