Trifluoroacetic acid → [4-(1H-indol-3-ylmethyl)-5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-acetic acid

Participants

Reaction Steps

To a solution of [4-(1H-indol-3-ylmethyl)-5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-acetic acid tert-butyl ester (4.26 g, 8.19 mmol) in CH2Cl2 (27 mL) was added TFA (9.5 mL, 0.123 mmol). The reaction was stirred at room temperature for 8 hours and was concentrated in vacuo. The residue was dissolved in CH2Cl2 (50 mL) and Et2O (15 mL) and was stirred for 24 hours. The precipitate was filtered and was washed with Et2O to provide 2.33 g of [4-(1H-indol-3-ylmethyl)-5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-acetic acid. 1H NMR (DMSO-d6) δ 10.79 (s, 1H), 7.70 (d, 1H), 7.54-7.38 (m, 7H), 7.26 (d, 1H), 7.17 (m, 2H), 6.98 (t, 1H), 6.88 (m, 2H), 4.90 (d, 1H), 4.49 (d, 1H), 3.82 (t, 1H), 3.59 (m, 2H).

Provenance & Evidence