Tetrahydrofuran → HCID 66833887, compound

HRID 61707Notes

Reaction equation

HRID 61707 reaction equation
C1COCC1.CC1(C)[O:11][CH:10]([CH2:12][O:13][C:14]2[CH:15]=[CH:16][C:17]3[C:29](=[O:30])[C:28]4[C:27]5[C:22](=[CH:23][C:24]([C:31]#[N:32])=[CH:25][CH:26]=5)[NH:21][C:20]=4[C:19]([CH3:34])([CH3:33])[C:18]=3[CH:35]=2)[CH2:9][O:8]1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>O>[OH:11][C@H:10]([CH2:9][OH:8])[CH2:12][O:13][C:14]1[CH:15]=[CH:16][C:17]2[C:29](=[O:30])[C:28]3[C:27]4[C:22](=[CH:23][C:24]([C:31]#[N:32])=[CH:25][CH:26]=4)[NH:21][C:20]=3[C:19]([CH3:34])([CH3:33])[C:18]=2[CH:35]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 66834064HCID 66834064, compound

Product 1

HCID 66833887HCID 66833887, compoundYield 106.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the solution of THF and water (4:1, 1 mL) of 8-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound A14-1, 30 mg, 0.07 mmol), camphor sulfonic acid (36 mg, 0.14 mmol) was added at room temperature. After stirring at room temperature for 38 hr, the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were purified by silica gel column chromatography (dichloromethane/methanol) to obtain the title compound (white solid, 28 mg, 72%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customThe drying agent was removed by filtration
  4. customthe residues obtained
  5. concentrationafter concentration under reduced pressure
  6. customwere purified by silica gel column chromatography (dichloromethane/methanol)

Sources & evidence

ORD record
ord-78979bafdffe4773932fc5b10a7bfc34
Source dataset
uspto-grants-2016_09
Patent number
US09440922B2

Reaction notes

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