反应详情

Same procedure as above with Z-Trp-NH(CH2)4NHBoc (1.16 g, 2.28 mmol), 10% Pd/C (242 mg) in MeOH/DMF (10 mL, 1/1). After purification by flash chromatography on silica gel (4-25% MeOH/CH2Cl2), Trp-NH(CH2)4NHBoc was isolated as a white foam (701 mg, 82%). 1H NMR (300 MHz, CDCl3) δ 1.39 (m, 4H, 2 CH2), 1.46 (s, 9H, (CH3)3), 3-3.35 (m, 6H, CH2 Trp, 2 CH2N), 3.7 (m, 1H, CHα), 4.71 (m, 1H, NHBoc), 7.05 (d, J=2 Hz, 1 aromatic H), 7.1 (t, J=7.7 Hz, 1 aromatic H), 7.2 (m, 2H, 1 aromatic H, NH amide), 7.38 (d, J=7.9 Hz, 1 aromatic H), 7.65 (d, J=7.9 Hz, 1 aromatic H), 8.94 (broad s, 1H, NH indole). 13C NMR (75 MHz, CDCl3) δ 26.9, 27.6, 30.8 (2 CH2, CH2 Trp), 28.5 ((CH3)3), 38.7, 40.3 (CH2NHCO, CH2NHBoc), 55.6 (CHα), 79.3 (C(CH3)3), 111.3, 111.4, 118.9, 119.5, 122, 123.3, 127.6, 136.4 (8 aromatic C), 156.2 (CO carbamate), 174.8 (CO amide).

1. customAfter purification by flash chromatography on silica gel (4-25% MeOH/CH2Cl2)