Potassium Carbonate → HCID 89472290, compound

HRID 514620

Reaction equation

[CH3:1][C:2]1([CH3:29])[O:7][CH2:6][C:5]([CH2:20][N:21]2[CH:25]=[CH:24][N:23]=[C:22]2[N+:26]([O-:28])=[O:27])([CH2:8]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:4][O:3]1.C1N2CCOCCOCCN(CCOCCOCC2)CCOCCOC1.[F-:56].[K+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:1][C:2]1([CH3:29])[O:7][CH2:6][C:5]([CH2:8][F:56])([CH2:20][N:21]2[CH:25]=[CH:24][N:23]=[C:22]2[N+:26]([O-:28])=[O:27])[CH2:4][O:3]1

Participants

Conditions

Temperature: 25 °C

Procedure

30 mg (0.0705 mmol equivalents) of 2,2-dimethyl-5-[(2-nitro-1H-imidazol-1-yl)methyl]-5-(p-toluenesulfonyloxymethyl)-1,3-dioxane was dissolved in 1.0 mL of acetonitrile, 39.8 mg (0.106 mmol equivalents) of Kryptofix 222 (trade name, Merck), 5.1 mg (0.088 mmol equivalents) of potassium fluoride, and 2.0 mg (0.014 mmol equivalents) of potassium carbonate were added thereto, and the mixture was stirred under reflux by heating for 3 hours. After completion of the reaction, the reaction liquid was cooled to room temperature (25° C.), the solvent was then removed by distillation, and the obtained crude product was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=2/1) to give 9.2 mg (0.034 mmol equivalents) of 2,2-dimethyl-5-fluoromethyl-5-[(2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxane.

Workup

temperatureunder reflux
temperatureby heating for 3 hours
customAfter completion of the reaction
customthe reaction liquid
customthe solvent was then removed by distillation
customthe obtained crude product
customwas purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=2/1)

Sources & evidence

ORD record: ord-d879485147614645b6791ae16e220054
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09107964B2

Linked notes

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