Cbz-Trp-NHBn → (S)-2-Amino-N-benzyl-3-(1H-indol-3-yl)propanamide

Participants

Reaction Steps

Same procedure as above with Z-Trp-NHCH2Ph (616 mg, 1.44 mmol), 10% Pd/C (153 mg) in MeOH/DMF (14.5 mL, 1/1). After purification by flash chromatography on silica gel (3-12% MeOH/CH2Cl2), Trp-NHCH2Ph was isolated as a pale yellow oil (351 mg, 83%). 1H NMR (300 MHz, CDCl3) δ 2.98 (dd, J=14.4 Hz, J=8.7 Hz, 1H, CH2), 3.44 (dd, J=14.4 Hz, J=4.1 Hz, 1H, CH2), 3.80 (dd, J=8.7 Hz, J=4.2 Hz, 1H, CHα), 4.46 (m, 2H, CH2 (Bn)), 7.06 (d, J=2.1 Hz, 1 aromatic H), 7.13-7.36 (m, 7 aromatic H), 7.41 (d, J=8 Hz, 1 aromatic H), 7.61 (m, 1H, NH amide), 7.72 (d, J=7.8 Hz, 1 aromatic H), 8.3 (broad s, 1H, NH indole). 13C NMR (75 MHz, MeOD) δ 30.5 (CH2 Trp), 42.7 (CH2 Ph), 55.4 (CHα), 109.3, 111, 118.1, 118.5, 121.2, 123.5, 126.8, 127, 127.1, 127.4, 128, 128.1, 136.8, 138 (14 aromatic C), 174.6 (CO amide).

Provenance & Evidence