Reaction Steps
To a solution of 5-hydroxy-3-amino-1-[S]-(chloromethyl)-1,2-dihydro-3H-benz(e)indole, hydrochloride salt (155 mg, 0.57 mmol) and 5-(3-(methyl-disulfanyl)propanamido)-1H-indole-2-carboxylic acid (170 mg, 0.55 mmol) in 7.0 ml of DMA was added EDC (300 mg, 1.56 mmol) under Ar. After stirred over night, the mixture was evaporated to dryness, purified by SiO2 chromatography (20% to 40% THF in toluene) and crystallized with THF/Toluene/Hexane to afford 218 mg (76%) of DC101SMe. 1H NMR (DMF-d7) 11.63 (s, 1H), 10.56 (s, 1H), 9.95 (s, 1H), 8.23 (s, 2H), 7.93 (d, 1H, J=8.3 Hz), 7.56 (dd, 1H, J=2.0, 8.1 Hz), 7.52 (s, 1H), 7.47 (dd, 1H, J=1.9, 8.9 Hz), 7.41 (d, 1H, J=1.7 Hz), 7.25 (d, 1H, J=1.7 Hz), 4.88 (dd, 1H, J=8.7, 11.0 Hz), 4.73 (dd, 1H, J=2.3, 10.9 Hz), 4.31 (m, 1H), 4.12 (dd, 1H, J=3.1, 11.0 Hz), 3.95 (dd, 1H, J=8.4, 11.2 Hz), 3.21 (t, 2H, J=7.1 Hz), 2.71 (t, 2H, J=7.1 Hz), 2.45 (s, 3H); 13C NMR 169.54, 161.06, 155.36, 134.21, 133.39, 132.54, 131.05, 128.39, 127.99, 123.98, 123.74, 123.46, 123.31, 118.88, 115.99, 112.87, 112.31, 106.40, 101.33, 55.93, 48.10, 42.61, 36.92, 30.81, 25.34. MS m/z+548.2 (M+Na), 550.2 (M+2+Na).
