Trifluoroacetic acid → 2-(N-(4-((4-(heptyloxy)benzoyl)oxy)benzyl)-4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)benzamido)acetic acid

Participants

Reaction Steps

Prepared using General Procedures 8: To 4-((N-(2-(tert-butoxy)-2-oxoethyl)-4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)benzamido)methyl)phenyl 4-(heptyloxy)benzoate INT-6 (555 mg, 0.702 mmol) in DCM (3 mL) was added TFA (3 mL). The reaction was stirred at room temperature for 2 h then purified by chromatography (EA/hexanes+1% acetic acid) to provide 385 mg (74%) of 2-(N-(4-((4-(heptyloxy)benzoyl)oxy)benzyl)-4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)benzamido)acetic acid 3. LCMS-ESI (m/z) calculated for C40H41F3N2O8: 734; no m/z observed, tR=11.42 min (Method 2). 1H NMR (400 MHz, DMSO) δ 12.83 (s, 1H), 10.35 (s, 1H), 8.14-8.01 (m, 2H), 7.65 (d, J=8.3 Hz, 2H), 7.54-7.29 (m, 5H), 7.29-7.16 (m, 4H), 7.14-7.01 (m, 2H), 4.69 (s, 1H), 4.61 (s, 1H), 4.08 (t, J=6.5 Hz, 2H), 4.00 (s, 1H), 3.94 (s, 1H), 3.86 (s, 2H), 3.83 (s, 3H), 1.81-1.68 (m, 2H), 1.48-1.22 (m, 8H), 0.92-0.81 (t, J=6.8 Hz, 3H).

Provenance & Evidence