Ethanol → HCID 136005907, compound

HRID 915954Notes

Reaction equation

HRID 915954 reaction equation
[CH2:1](O)C.[CH:4]1([C:10]2[C:18]3[C:17](=[O:19])[NH:16][C:15]([C:20]4[CH:25]=[CH:24][C:23]([N:26]5[CH2:32][CH2:31][CH2:30][NH:29][CH2:28][CH2:27]5)=[CH:22][C:21]=4[O:33][CH3:34])=[N:14][C:13]=3[N:12]([CH3:35])[N:11]=2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.C=O.C(=O)([O-])O.[Na+]>C(O)=O>[CH:4]1([C:10]2[C:18]3[C:17](=[O:19])[NH:16][C:15]([C:20]4[CH:25]=[CH:24][C:23]([N:26]5[CH2:32][CH2:31][CH2:30][N:29]([CH3:1])[CH2:28][CH2:27]5)=[CH:22][C:21]=4[O:33][CH3:34])=[N:14][C:13]=3[N:12]([CH3:35])[N:11]=2)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1

Participants

6

Reactant 4

HCID 702EthanolHCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 136005859HCID 136005859, compound

Product 1

HCID 136005907HCID 136005907, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To a 2 ml ethanol/2 ml water mixed solution of 60 mg (0.14 mmol) of the compound obtained in Example 133, 30 mg of paraformaldehyde and 1 ml of formic acid were added, and the mixture was heated under reflux for 24 hours. Then, the reaction mixture was brought to room temperature, an aqueous solution of sodium hydrogen carbonate was added, and the mixture was extracted with dichloromethane. The organic layer was washed with water and a saturated aqueous solution of sodium chloride. After the washed layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=10/1) to obtain 53 mg (84%) of the captioned compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 24 hours
  3. customwas brought to room temperature
  4. extractionthe mixture was extracted with dichloromethane
  5. washThe organic layer was washed with water
  6. dry with materialAfter the washed layer was dried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-49ecc507c81d4636b630e2d3c262844d
Source dataset
uspto-grants-2007_09
Patent number
US07268128B2

Reaction notes

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