Benzoic Acid → HCID 178486781, compound

HRID 1443471Notes

Reaction equation

HRID 1443471 reaction equation
C(O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC[N:12]=[C:13]=[N:14][CH2:15][CH2:16][CH2:17]N(C)C.[C:21](O)(=O)[CH2:22][C:23]([CH2:28]C(O)=O)(C(O)=O)O.[C:34](=[O:37])([O-])[O-].[Na+].[Na+].CN([CH:43]=[O:44])C>BrCC(=O)C(C)C>[CH3:43][O:44][C:17]1[CH:16]=[C:15]2[C:21]([C:34]([OH:37])=[N:12][C:13]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[N:14]2)=[CH:22][C:23]=1[CH3:28]

Participants

7

Reactant 5

HCID 243Benzoic AcidHCID 311Citric Acid2×HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide

Product 1

HCID 178486781HCID 178486781, compound

Reagents, catalysts & solvents 1

HCID 108990371-Bromo-3-methylbutan-2-oneSolvent

Procedure

To a mixture of compound III (1.8 g, 10 mmol), benzoic acid (1.46 g, 12 mmol) and hobt-hydrate (1.87 g, 12 mmol) in dry DMF (60 ml) was added EDAC (2.4 g, 12.5 mmol) and TEA (1.75 ml, 12.5 mmol) and the mixture was stirred at room temperature for 60 h. 5% Citric acid was added and the mixture was evaporated three times with ethyl acetate. The organic phase was washed with brine and saturated sodium hydrogen carbonate solution. The organic phase was dried with sodium sulphate and evaporated under reduced pressure. The residue was refluxed for two hours with sodium carbonate (2.65 g, 25 mmol) in 100 ml ethanol-water 1/1.5% Citric acid was added and the mixture was extracted three times with ethyl acetate including 10% THF. Silica gel was added, the solvent was evaporated and the product was purified by column chromatography on silica gel eluted with hexane-ethyl acetate.

Workup

  1. customthe mixture was evaporated three times with ethyl acetate
  2. washThe organic phase was washed with brine and saturated sodium hydrogen carbonate solution
  3. dry with materialThe organic phase was dried with sodium sulphate
  4. customevaporated under reduced pressure
  5. additionwas added
  6. extractionthe mixture was extracted three times with ethyl acetate including 10% THF
  7. additionSilica gel was added
  8. customthe solvent was evaporated
  9. customthe product was purified by column chromatography on silica gel
  10. washeluted with hexane-ethyl acetate

Sources & evidence

ORD record
ord-d07c3feeb5924ddabe44a3c14e17f224
Source dataset
uspto-grants-2010_02
Patent number
US07659245B2

Reaction notes

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