Reaction Steps
compound SP306P. Same procedure as above with Trp-NHPh (99.6 mg, 0.356 mmol), N-Boc-Tyr(Bn)-Lys(Boc)-OH (214 mg, 0.356 mmol), EDC (75.3 mg, 0.392 mmol) and HOBt (53.7 mg, 0.397 mmol) in CH2Cl2/DMF (1.5 mL, 1/1). The crude residue was triturated with MeOH/pentane to afford a white solid (193.5 mg, 63%). 1H NMR (300 MHz, DMSO-d6) δ 1.21-1.62 (m, 6H, 3 CH2 Lys), 1.3 (s, 9H, (CH3)3), 1.36 (s, 9H, (CH3)3), 2.64 (m, 1H, CH2 Tyr), 2.87 (m, 3H, CH2 Lys, CH2 Tyr), 3.05 (dd, J=14.7 Hz, J=7.7 Hz, 1H, CH2 Trp), 3.19 (dd, J=14.7 Hz, J=6.2 Hz, 1H, CH2 Trp), 4.11 (m, 1H, CHα), 4.31 (m, 1H, CHU), 4.71 (m, 1H, CHU), 5.02 (s, 2H, CH2 (Bn)), 6.71 (m, 1H), 6.87-7.42 (m, 17H), 7.58 (m, 3H), 7.9 (d, J=7.3 Hz, 1H), 8.18 (d, J=7.2 Hz, 1H), 10 (s, 1H), 10.8 (s, 1H). 13C NMR (75 MHz, DMSO-d6) δ 22.5, 29.2, 32 (3 CH2 Lys), 27.8 (CH2 Trp), 28.1, 28.2 (2 (CH3)3), 36.3 (CH2 Tyr), 39.8 (CH2 Lys), 52.4, 54.2, 55.8 (CHα Tyr, Lys, Trp), 69.1 (CH2 (Bn)), 77.3, 78.1 (2 C(CH3)3), 109.6, 111.2, 114.3, 118.2, 118.4, 119.4, 120.8, 123.3, 123.4, 127.3, 127.5, 127.7, 128.3, 128.6, 130.1, 130.2, 136, 137.2, 138.8 (25 aromatic C), 155.2, 155.5, 156.8 (Car-O, 2 CO carbamate), 170.1, 171.5, 171.6 (3 CO amide). Anal. Calcd. for C49H60N6O8, 1.5H2O: C, 66.27; H, 7.15; N, 9.46. Found: C, 66.42; H, 6.96; N, 9.34.
