Sodium Hydroxide → HCID 66782728, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl rac-(5R,6S)-13-cyclohexyl-10-((((dimethylamino)sulfonyl)amino)carbonyl)-5,6-dihydroxy-3-(methyloxy)-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-6-carboxylate (57 mg, 0.10 mmol) in MeOH/THF (1:1, 2 mL) was added 1M NaOH aq. (0.5 mL). The reaction was sealed and heated at 80° C. for 20 min with microwave irradiation. The reaction was quenched with 1N HCl aq. (0.5 mL), diluted with H2O and concentrated to remove the organic solvents. The resulting precipitates were collected by filtration and dried under vacuum to yield rac-(5R,6S)-13-cyclohexyl-10-((((dimethylamino)sulfonyl)amino)carbonyl)-5,6-dihydroxy-3-(methyloxy)-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-6-carboxylic acid (42 mg, 0.074 mmol, 73%) as a yellow solid. 1HNMR (300 MHz, CD3OD) δ 0.73-2.20 (m, 10H), 2.92-3.05 (m, 1H), 3.02 (s, 6H), 3.54 (d, J=14.8 Hz, 1H), 3.93 (s, 3H), 4.71 (d, J=14.8 Hz, 1H), 4.94 (s, 1H), 7.05 (dd, J=8.4, 2.6 Hz, 1H), 7.40 (d, J=2.6 Hz, 1H), 7.40 (d, J=8.4 Hz, 1H), 7.59 (dd, J=8.4, 1.5 Hz, 1H), 7.89 (d, J=8.4 Hz, 1H), 8.05 (d, J=1.5 Hz, 1H). LCMS: m/e 572 (M+H)+, ret time 3.34 min, column B, 4 minute gradient.

Provenance & Evidence