Sulfuric Acid → HCID 66835037, compound

HRID 61844Notes

Reaction equation

C1COCC1.[Br:6][C:7]1[CH:19]=[C:18]2[C:10]([C:11]3[C:12](=[O:36])[C:13]4[CH:26]=[CH:25][C:24]([O:27][CH2:28][C@H:29]5[CH2:33][O:32]C(C)(C)[O:30]5)=[CH:23][C:14]=4[C:15]([CH3:22])([CH3:21])[C:16]=3[N:17]2[CH3:20])=[CH:9][CH:8]=1.S(=O)(=O)(O)O.C(=O)([O-])O.[Na+]>C(OCC)C.CO>[Br:6][C:7]1[CH:19]=[C:18]2[C:10]([C:11]3[C:12](=[O:36])[C:13]4[CH:26]=[CH:25][C:24]([O:27][CH2:28][C@H:29]([OH:30])[CH2:33][OH:32])=[CH:23][C:14]=4[C:15]([CH3:21])([CH3:22])[C:16]=3[N:17]2[CH3:20])=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 55 °C

Procedure

Under nitrogen atmosphere, to the THF (0.15 mL)-MeOH (0.1 mL) solution of 3-bromo-8-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl methoxy)-5,6,6-trimethyl-5,6-dihydro-benzo[b]carbazol-11-one (Compound T24-1, 15.5 mg, 0.0320 mmol), 0.5 M aqueous solution of sulfuric acid (128 μL, 0.0640 mmol) was added at room temperature. The reaction mixture was stirred at ambient temperature of 55° C. for 2 hr, cooled to room temperature, and then added with diethyl ether and subsequently with sodium hydrogen carbonate (11 mg). The mixture was extracted twice with diethyl ether/ethyl acetate, and the organic layer was washed with brine, dried over sodium sulfate and concentrated under reduced pressure to obtain the title compound (white solid, 11.9 mg, 84%).

Workup

temperaturecooled to room temperature
extractionThe mixture was extracted twice with diethyl ether/ethyl acetate
washthe organic layer was washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-ecd2fbfa059c4972bbfb15e65b906aa8
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440922B2

Reaction notes

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