Sodium Carbonate → (S)-2-(Tert-butoxycarbonylamino)-3-(3'-chlorobiphenyl-4-yl)propanoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of Boc-4-bromo-L-phenylalanine (15 g, 43.6 mmol) in DME (180 ml) at room temperature was added 3-chlorobenzeneboronic acid (8.52 g, 54.5 mmol) followed by aq. Na2CO3 (32.7 ml, 65.4 mmol) and Pd(PPh3)4 (1.511 g, 1.307 mmol). The mixture was stirred at 85° C. for 3 hours. The reaction mixture was filtered and added EtOAc and acidified by 1M HCl to pH˜5. The combined organic layer was washed with brine and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The obtained residue was purified by flash chromatography (silica gel, 5 to 20% EtOAc/Heptane) and gave the title compound: 12.0 g (yield: 66%). LCMS (condition A): 374.2 (M−1); retention time=1.57 min.

Provenance & Evidence