Trifluoroacetic acid → 2-(2-methoxy-4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)-N-(4-((4'-methyl-[1,1'-biphenyl]-4-carbonyl)oxy)benzyl)benzamido)acetic acid

Participants

Reaction Steps

Prepared using General Procedures 2 then 8: To a stirring suspension of 4′-methyl-[1,1′-biphenyl]-4-carboxylic acid (57 mg, 0.27 mmol) in DCM (5 mL) were added DMF (2 drops) and oxalyl chloride (25 μL, 0.29 mmol). The reaction mixture was stirred at room temperature for 2 h. To this mixture was added a solution of tert-butyl 2-(N-(4-hydroxybenzyl)-2-methoxy-4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)benzamido)acetate INT-24 (108 mg, 0.18 mmol) and TEA (62 μL, 0.45 mmol) in DCM (5 mL). The reaction mixture was stirred at room temperature for 2 h then TFA (3 mL) was added. After stirring for 2 h, the solvent was concentrated and the product was purified by preparative HPLC to provide to afford 23.1 mg (17%) of 2-(2-methoxy-4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)-N-(4-((4′-methyl-[1,1′-biphenyl]-4-carbonyl)oxy)benzyl)benzamido)acetic acid 314 as a white powder. LCMS-ESI (m/z) calculated for C41H35F3N2O8: 740; found 741 [M+H]+, tR=10.33 min (Method 9). 1H NMR (400 MHz, DMSO) δ 12.77 (s, 1H), 10.34 (s, 0.5H), 10.32 (s, 0.5H), 8.25-8.15 (m, 2H), 7.93-7.85 (m, 2H), 7.74-7.64 (dt, J=6.3, 2.3 Hz, 2H), 7.53-7.39 (m, 3H), 7.39-7.07 (m, 9H), 5.01 (br s, 1H), 4.42 (s, 1H), 3.90-3.65 (m, 10H), 2.38 (s, 3H).

Provenance & Evidence