Acetic Acid → (R)-6-[[3-[[4-[2-[[2-[8-(Benzyloxy)-2-oxo-1,2-dihydroquinolin-5-yl]-2-hydroxyethyl]amino]ethyl]-phenyl]carbamoyl]phenyl]sulfonyl]-4-[(3-methoxyphenyl)amino]-8-methylquinoline-3-carboxamide

Participants

Reaction Steps

Intermediate 140 (135 mg, 0.133 mmol) was combined with TBAF (1M/THF, 0.4 mL) and acetic acid (23 μL) in anhydrous acetonitrile (0.2 mL) and allowed to stir at rt. After 18 h, the reaction was concentrated in vacuo to a brown oil, which was suspended in H2O. The solid was filtered and washed with H2O and hexane, then dried to give the title compound as a yellow solid, 124 mg, which was used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6) δ 10.80 (s, 1H), 10.46 (s, 1H), 9.09 (s, 1H), 8.37 (s, 1H), 8.32 (s, 1H), 8.30 (br s, 1H), 8.16-8.24 (m, 2H), 8.03 (s, 1H), 7.86 (d, J=7.9 Hz, 1H), 7.77 (br s, 1H), 7.76 (dd, J=7.6, 15.6 Hz, 1H), 7.66 (d, J=8.3 Hz, 2H), 7.55 (d, J=7.6 Hz, 2H), 7.32-7.41 (m, 2H), 7.26-7.32 (m, 1H), 7.07-7.23 (m, 5H), 6.61-6.69 (m, 2H), 6.49-6.59 (m, 2H), 5.28 (s, 2H), 5.03 (t, J=6.1 Hz, 1H), 3.60 (s, 3H), 3.15-3.19 (m, 2H), 2.70 (s, 3H), 2.62-2.81 (m, 7H). ES/MS calcd. for C51H47N6O8S+ 903.3. Found m/z=903.3 (M+H+).

Provenance & Evidence