4-(2-Carboxyethyl)benzeneboronic acid → 3-[3',5'-Dichloro-4'-(1-cyclohexyl-2-oxo-pyrrolidin-3-ylmethyl)-biphenyl-4-yl]-propionic acid

Participants

Reaction Conditions

Reaction Steps

Charge a vial with 3,5-dichloro-4-((1-cyclohexyl-2-oxopyrrolidin-3-yl)methyl)phenyl trifluoromethanesulfonate (Example 240) (0.30 g, 0.63 mmol), 4-(2-carboxyethyl)benzene boronic acid (0.123 g, 0.634 mmol) and Pd(Ph3)4 (0.073 g, 0.063 mmol) in 1,4-dioxane (5 mL) and 2 M Na2CO3 (1 mL) and heat to 95° C. for 16 hours. Cool the reaction, extract with ethyl acetate and water, dry the organic layer (Na2SO4) and purify by HPLC (5 to 95% acetonitrile in water with 0.1% trifluroacetic acid buffer) to afford 373 mg (62%) of the title compound: LC-MS (ES +) m/z=exact mass calcd for C26H29Cl2NO3 473, found 474 and 476 (M+1 and M+3, 100%).

Provenance & Evidence