3-Tolylboronic acid → Boc-4-(3-methylphenyl)-L-phenylalanine

Participants

Reaction Steps

(S)-3-(4-bromophenyl)-2-(tert-butoxycarbonylamino)propanoic acid (2.0 g, 5.81 mmol), 3-methylphenylboronic acid (0.948 g, 6.97 mmol), Pd(PPh3)4 (0.336 g, 0.291 mmol) and 2M NaCO3 aqueous solution (4.36 mL) were stirred in 1,2-dimethoxyethane (30 mL) at 80° C. for 2.5 hours. After being cooled to room temperature, the reaction mixture was diluted with EtOAc and washed with 1M HCl and brine. The organic layer was dried over Na2SO4, concentrated under reduced pressure, and purified by silica gel flash column chromatography (10% MeOH in DCM/DCM) to give(S)-2-(tert-butoxycarbonylamino)-3-(3′-methylbiphenyl-4-yl)propanoic acid. MS: m/z (MH+-Boc) 256. Retention time=1.45 min. (condition A).

Provenance & Evidence