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

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Reaction Steps

Prepared using General Procedure 8: To crude 4-((N-(2-(tert-butoxy)-2-oxoethyl)-4-(2-(4-methoxyphenyl)acetamido)benzamido)methyl)phenyl 4-(heptyloxy)benzoate INT-5 (70 mg) was added TFA (1 mL). After stirring for 1 h, the solvent was concentrated and the product was purified by preparative HPLC to provide 19 mg (23%) of 2-(N-(4-((4-(heptyloxy)benzoyl)oxy)benzyl)-4-(2-(4-methoxyphenyl)acetamido)benzamido)acetic acid 1. LCMS-ESI (m/z) calculated for C39H42N2O8: 667; found 666 [M−H]−, tR=9.51 min (Method 4). 1H NMR (400 MHz, DMSO) δ 12.80 (s, 1H), 10.31 (s, 1H), 8.16-7.97 (m, 2H), 7.69-7.58 (d, J=8.5 Hz, 2H), 7.48-7.27 (m, 4H), 7.28-7.19 (d, J=8.1 Hz, 4H), 7.15-7.05 (m, 2H), 6.93-6.82 (d, J=8.1 Hz, 2H), 4.74-4.51 (d, J=35.4 Hz, 2H), 4.15-3.80 (m, 4H), 3.71 (s, 3H), 3.66 (s, 2H), 1.84-1.66 (m, 2H), 1.48-1.19 (m, 8H), 0.93-0.80 (t, J=6.6 Hz, 3H).

Provenance & Evidence