Potassium Carbonate → HCID 57474918, compound

HRID 1929396Notes

Reaction equation

HRID 1929396 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-aca7e75f816944948e76ba5d0bc9f668
Source dataset
uspto-grants-2012_05
Patent number
US08188077B2

Reaction notes

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