Reaction #41907

Reaction equation

(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

Yield 20.7%

Solvents

DCM

ethyl acetate

Conditions

Workup

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

Procedure

(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.

Source