(E)-7-Pyridin-3-yl-hept-6-enoic acid → (RS)-5-(4-Benzyloxy-phenyl)-4-(7-pyridin-3-yl-heptanoylamino)-pentanoic acid methyl ester

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Isolated as a gum from (E)-7-Pyridin-3-yl-hept-6-enoic acid 76 (137 mg, 0.67 mmol) and (RS)-5-(4-Benzyloxy-phenyl)-4-tertbutoxycarbonylamino-pent-2-enoic acid methyl ester RS-40 (250 mg, 0.61 mmol) to afford the title compound (79.4 mg, 26%) as a gum: chromatographed on silica using 70:30 EtOAc:petroleum. 1H nmr (CDCl3) δ 1.30 (m, 4H), 1.49-1.82 (m, 5H), 1.82-1.95 (m, 1H), 2.08 (t, J=8 Hz, 2H), 2.34 (m, 2H), 2.59 (t, J=8 Hz), 2.69 (dd, J=7, 14 Hz, 1H), 2.77 (dd, J=7, 14 Hz, 1H), 3.65 (s, 3H), 4.15 (m, 1H), 5.03 (s, 2H), 5.36 (br d, J=9 Hz, 1H), 6.90 (d, J=9 Hz, 2H), 7.9 (d, J=9 Hz, 2H), 7.17-7.52 (m, 7H), 8.42 (br s, 2H). ESMS 503 (M+H)+.

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