Potassium Carbonate → HCID 57474918, compound

HRID 1798429Notes

Reaction equation

HRID 1798429 reaction equation
[CH:1]12[CH2:18][CH:5]([N:6]([C:8]([O:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:9])[CH2:7]1)[CH2:4][CH2:3][NH:2]2.F[C:20]1[CH:30]=[CH:29][C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O>[CH2:27]([O:26][C:24]([C:23]1[CH:29]=[CH:30][C:20]([N:2]2[CH2:3][CH2:4][CH:5]3[CH2:18][CH:1]2[CH2:7][N:6]3[C:8]([O:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:9])=[CH:21][CH:22]=1)=[O:25])[CH3:28]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 67976Benzoic acid, 4-fluoro-, ethyl esterHCID 57474919HCID 57474919, compound

Product 1

HCID 57474918HCID 57474918, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

Benzyl 2,6-diazabicyclo[3.2.1]octane-6-carboxylate (300 mg) was dissolved in dimethylsulfoxide (3 mL), then ethyl 4-fluorobenzoate (172 mg) and potassium carbonate (206 mg) were added. The reaction was heated at 130° C. overnight. After cooling, the reaction was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. After filtration and concentration of the filtrate, the resultant crude material was purified by column chromatography on silica gel using 7/3 hexanes/ethyl acetate to afford the title compound.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtration and concentration of the filtrate
  6. customthe resultant crude material was purified by column chromatography on silica gel using 7/3 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-ebfe0b471d86471c989b03e3ba68b1ed
Source dataset
uspto-grants-2013_01
Patent number
US08343967B2

Reaction notes

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