Reaction Steps
Same procedure as above with Z-Trp-OH (2 g, 5.9 mmol), benzylamine (645 μL, 5.9 mmol), DCC (1.58 g, 7.65 mmol) and THF (88 mL). A white solid was obtained after precipitation in methanol/pentane (777 mg, 31%). 1H NMR (300 MHz, CDCl3) δ 3.18 (dd, J=14.3 Hz, J=8.1 Hz, 1H, CH2), 3.39 (dd, J=14.3 Hz, J=4.9 Hz, 1H, CH2), 4.3 (m (AB), 2H, CH2 (Bn)), 4.53 (m, 1H, CHα), 5.11 (s, 2H, CH2 (Z)), 5.52 (m, 1H, NH), 5.90 (m, 1H, NH), 6.91-7.70 (m, 15 aromatic H), 8.01 (s, 1H, NH indole). 13C NMR (75 MHz, CDCl3) δ 28.7 (CH2 Trp), 43.4 (CH2), 56.1 (CHα), 67 (CH2 (Z)), 111.2, 118.7, 119.7, 122.2, 123.2, 123.4, 127.2, 127.3, 127.6, 128, 128.2, 128.5, 136.1, 136.2, 137.5, 137.6 (20 aromatic C), 156 (CO carbamate), 171.2 (CO amide). Anal. Calcd. for C26H25N3O3, 0.75H2O: C, 70.81; H, 6.06; N, 9.53. Found: C, 70.84; H, 6.80; N, 9.21.
