Реакция #41907

Уравнение реакции

(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionic acid methyl ester

4-pyridyl boronic acid

Triethylamine

→

(S)-2-tert-Butoxycarbonylamino-3-[4-(pyridin-4-yloxy)-phenyl]-propionic acid methyl ester

Выход 20.7%

Растворители

DCM

ethyl acetate

Условия реакции

Обработка

1. 1
   Промывкаwashed with 10% sodium carbonate (6×)
2. 2
   ДругоеThe organic layer was dried
3. 3
   Концентрированиеconcentrated under reduced pressure
4. 4
   ДругоеThe residue was purified over silica gel (hexanes-EtOAc)

Методика

(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionic acid methyl ester (8.46 mmol), 4-pyridyl boronic acid (29.6 mmol), Cu(OAc)2 (16.9 mmol), and molecular sieves were suspended in 25 mL of DCM. Triethylamine (59.2 mmol) was added and the mixture stirred at rt for 10 h. The mixture was diluted with ethyl acetate and washed with 10% sodium carbonate (6×). The organic layer was dried and concentrated under reduced pressure. The residue was purified over silica gel (hexanes-EtOAc) to provide (S)-2-tert-Butoxycarbonylamino-3-[4-(pyridin-4-yloxy)-phenyl]-propionic acid methyl ester (653 mg). LC-MS (m/z) 374.

Источник