HCID 67296679, compound → HCID 67313472, compound

Participants

Reaction Steps

A solution of (E)-tert-butyl 3-(3-(2-propylpentanamido)phenyl)allylcarbamate (0.5 g, 1.32 mmol) in ethanol was degassed by bubbling argon for 2 min. Pd/C (10% wt, 0.5 g) was added and the reaction mixture atmosphere was changed to hydrogen by alternating between vacuum and hydrogen 2×. The reaction mixture was stirred under a H2-filled balloon for 16 h then filtered through Celite and the filtrate was concentrated under reduced pressure. Purification by column chromatography (100-200 mesh silica, 10% to 15% EtOAc in hexane) gave compound tert-butyl 3-(3-(2-propylpentanamido)phenyl)propylcarbamate as a thick yellow oil. Yield (0.5 g, 99%); 1H NMR (400 MHz, CDCl3) δ 7.45 (s, 1H), 7.31 (d, J=7.6 Hz, 1H), 7.22 (t, J=8.0 Hz, 1H), 7.08 (bs, 1H), 6.93 (d, J=7.6 Hz, 1H), 4.60 (bs, 1H), 3.15-3.14 (m, 2H), 2.62 (t, J=7.2 Hz, 2H), 2.49-2.16 (m, 1H), 1.82-1.72 (m, 2H), 1.72-1.66 (m, 2H), 1.37 (s, 9H), 1.36-1.22 (m, 6H), 0.92 (t, J=7.2 Hz, 6H).

Provenance & Evidence