反应详情

A Schlenk flask charged with Z-Trp-NHPh (1.7 g, 4.11 mmol) and 10% Pd/C (437.4 mg) was flushed under H2 before adding MeOH/DMF (41 mL, 1/1). The reaction mixture was stirred under atmosphere of H2 overnight followed by filtration through a pad of celite. The solvent was removed in vacuo and the crude was purified by flash column chromatography on silica gel (2-8% MeOH/CH2Cl2). The amine was isolated as a yellow solid (841 mg, 73%). mp 114-116° C. 1H NMR (300 MHz, CDCl3) δ 1.89 (broad s, 2H, NH2), 3.06 (dd, J=14.5 Hz, J=8.8 Hz, 1H, CH2), 3.55 (dd, J=14.5 Hz, J=3.9 Hz, 1H, CH2), 3.89 (dd, J=8.8 Hz, J=3.8 Hz, 1H, CHα), 7.06-7.41 (m, 7 aromatic H), 7.61 (d, J=7.9 Hz, 2 aromatic H), 7.72 (d, J=7.8 Hz, 1 aromatic H), 8.24 (broad s, 1H, NH amide), 9.48 (s, 1H, NH indole). 13C NMR (75 MHz, CDCl3) δ 30.5 (CH2 Trp), 56 (CHα), 111.4, 118.8, 119.5, 119.7, 122.3, 123.2, 124.1, 127.5, 129, 129.1, 136.5, 137.8 (14 aromatic C), 173.2 (CO amide).

1. customwas flushed under H2
2. additionbefore adding MeOH/DMF (41 mL, 1/1)
3. filtrationfollowed by filtration through a pad of celite
4. customThe solvent was removed in vacuo
5. customthe crude was purified by flash column chromatography on silica gel (2-8% MeOH/CH2Cl2)