Ethanol → 3-(4'-Benzo[1,3]dioxol-5-yl-biphenyl-4-ylmethylsulfanyl)-2-tert-butoxycarbonyl amino-propionic Acid Methyl Ester

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-(4′-bromobiphenyl-4-ylmethylsulfanyl)-2-tert-butoxycarbonylamino-propionic acid methyl ester, 0.26 g (0.54 mmol), 3,4-methylenedioxyphenylboronic acid, 90 mg (0.54 mmol), Pd(PPh3)4, 63 mg (0.054 mmol), in 5 mL of toluene and 3 mL of ethanol was heated to obtain a clear solution. To the solution was added 5 mL of 0.4M aq. Na2CO3. The reaction mixture refluxed for 4 h at 80° C. The mixture was cooled to room temperature and diluted with 100 mL ethyl acetate. The organic layer was washed with 2×50 mL portions of water, 2×50 mL portions of sat. aq. NaCl, and dried (MgSO4). After the solution was concentrated, the residue was purified by column chromatography (eluted with 7% EtOAc-Heptane) to afford the desired product in 0.13 g (46%) as a white solid. 1H NMR (CDCl3) 7.64-7.56 (m, 6H), 7.38 (d, 2H, J=9.3 Hz), 7.10 (dd, 2H, J=6.7, 2.0 Hz), 6.90 (d, 1H, J=9.3 Hz), 6.01 (s, 2H), 5.32 (d, 1H, J=8.0 Hz), 4.63-4.52 (m, 1H), 3.78 (s, 2H), 3.76 (s, 3H), 2.95 (dd, 1H, J=15.7, 5.3 Hz), 2.85 (dd, 1H, J=15.7, 6.3 Hz), 1.47 (s, 9H).

Provenance & Evidence