Z-Trp-NHPh → (S)-2-Amino-3-(1H-indol-3-yl)-N-phenylpropanamide
Reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:13]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1>[Pd]>[NH2:1][C@H:2]([C:13]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
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).