Sulfuric Acid → HCID 178472735, compound

HRID 1893571Notes

Reaction equation

HRID 1893571 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH2:5][N:6]([CH2:24][C:25]([OH:27])=[O:26])[C:7]1[CH:15]=[C:14]2[C:10]([C:11]([CH3:22])=[N:12][N:13]2C2CCCCO2)=[CH:9][C:8]=1[CH3:23])[CH3:2].S(=O)(=O)(O)O>C(O)C>[CH2:1]([O:3][C:4](=[O:28])[CH2:5][N:6]([CH2:24][C:25]([OH:27])=[O:26])[C:7]1[CH:15]=[C:14]2[C:10]([C:11]([CH3:22])=[N:12][NH:13]2)=[CH:9][C:8]=1[CH3:23])[CH3:2]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 66881042HCID 66881042, compound

Product 1

HCID 178472735HCID 178472735, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The compound (2.53 g, 6.06 mmol) of step D was dissolved in ethanol (75 ml), concentrated sulfuric acid (0.5 ml) was added at room temperature, and thereafter the mixture was heated under reflux for 70 min. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate. The organic layer was washed with sodium bicarbonate water and saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, the solution was concentrated under reduced pressure, and the obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane) to give the title compound (1.72 g, yield 85%) as a yellow oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 70 min
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionthe residue was diluted with ethyl acetate
  5. washThe organic layer was washed with sodium bicarbonate water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationThe insoluble material was filtered off
  8. concentrationthe solution was concentrated under reduced pressure
  9. customthe obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-709119dfe7fb4cac89d0ade9c2e3094e
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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