反应详情

Suzuki coupling: To a solution of (S)-3-(4-Bromo-phenyl)-2-tert-butoxycarbonylamino-propionic acid methyl ester (70.1 mmol) in toluene (250 mL) was added 4-cyanobenzeneboronic acid (105 mmol), Pd(PPh3)4 (3.5 mmol), and 1N Na2CO3 solution (105 mL). The mixture was heated at reflux for 7 h. After completion of the reaction, the aqueous layer was drained. The organic was washed with 10% Na2CO3 and 1 N HCl. The organic was dried over sodium sulfate and concentrated under reduced pressure to afford the crude product. The residue was purified by column chromatography (hexanes-EtOAc) to provide (S)-2-tert-Butoxycarbonylamino-3-(4′-cyano-biphenyl-4-yl)-propionic acid methyl ester (18.2 g). LC-MS (m/z) 382.

1. temperatureThe mixture was heated
2. temperatureat reflux for 7 h
3. customAfter completion of the reaction
4. washThe organic was washed with 10% Na2CO3 and 1 N HCl
5. dry with materialThe organic was dried over sodium sulfate
6. concentrationconcentrated under reduced pressure
7. customto afford the crude product
8. customThe residue was purified by column chromatography (hexanes-EtOAc)