Formic Acid → HCID 23155527, compound

HRID 2080879Notes

Reaction equation

HRID 2080879 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]([CH2:20][CH2:21][CH3:22])[CH2:17][CH2:18][CH3:19])=[CH:6][CH:5]=1.C=O.[CH:26](O)=O>C(O)C>[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]([CH2:12][CH2:13][CH2:14][CH2:15][N:16]([CH2:17][CH2:18][CH3:19])[CH2:20][CH2:21][CH3:22])[CH3:26])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 712FormaldehydeHCID 67103860HCID 67103860, compound

Product 1

HCID 23155527HCID 23155527, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The compound (310 mg) obtained in Example 88-1 was dissolved in ethanol (4.5 ml) and added with a 36% formaldehyde aqueous solution (150 μl) and formic acid (175 μl) and the whole was refluxed for 2 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. The residue was dissolved in chloroform and washed with a 1 mol/l sodium hydroxide aqueous solution, followed by extraction with chloroform. The organic layer was washed with a saturated saline solution and dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure. The residue was purified through silica gel column chromatography (hexane/ethyl acetate), thereby obtaining the subject compound (234 mg) as a colorless oily substance.

Workup

  1. temperaturethe whole was refluxed for 2 hours
  2. customAfter completion of the reaction
  3. distillationthe solvent was distilled off under reduced pressure
  4. dissolutionThe residue was dissolved in chloroform
  5. washwashed with a 1 mol/l sodium hydroxide aqueous solution
  6. extractionfollowed by extraction with chloroform
  7. washThe organic layer was washed with a saturated saline solution
  8. dry with materialdried with anhydrous sodium sulfate
  9. filtrationAfter filtration
  10. distillationthe solvent was distilled off under reduced pressure
  11. customThe residue was purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-80052c610e55400fac6175beef13e3e7
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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