Reaction Steps
Using the above procedure Linoleic acid (2.80 g, 10.5 mmol) was coupled with the amine 100 (6.10 g, 11.45 mmol) using HBTU (4.55 g, 1.2 eq.) and DIEA (5.21 mL, 3.00 eq). After work-up and column purification the pure amide 102g was isolated as pale yellow gummy liquid (Yield, 6.10 g, 78%). 1H NMR (DMSO-d6, 400 MHz) δ=7.71-7.67 (m, 1H), 7.33-7.25 (m, 4H), 7.23-7.13 (m, 5H), 6.87-6.80 (m, 4H), 5.35-5.24 (m, 4H), 4.97 (d, J=3.90 Hz, 1H), 4.88 (d, J=3.90 Hz, 1H), 4.39-4.05 (m, 2H), 3.72 (s, 6H), 3.58-3.41 (m, 1H), 3.32-3.12 (m, 2H), 3.01-2.93 (m, 3H), 2.72-2.67 (m, 2H), 2.20-1.80 (m, 9H), 1.46-1.08 (m, 23H), 0.83 (t, J=6.34 Hz, 3H). 13C NMR (DMSO-d6, 400 MHz) δ=176.63, 170.97, 170.86, 162.22, 158.09, 157.97, 145.07, 144.73, 135.87, 135.73, 135.48, 135.43, 129.60, 129.57, 129.55, 127.81, 127.71, 127.57, 127.55, 126.69, 126.53, 113.15, 113.07, 113.06, 85.79, 85.12, 68.61, 67.47, 63.36, 55.07, 55.01, 54.96, 54.93, 38.60, 38.56, 38.29, 38.18, 38.02, 36.30, 36.16, 36.01, 35.71, 34.17, 32.55, 30.70, 29.06, 29.02, 27.73, 27.70, 27.53, 26.08, 26.04, 24.49, 24.10.
