Ethanol → HCID 66881861, compound

HRID 1893593Notes

Reaction equation

HRID 1893593 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][N:2]1[N:10]([CH3:35])[C:11](=[O:34])[CH2:12][N:13]([C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][C:26]=1[CH3:27])[N:23](C1CCCCO1)[N:22]=[CH:21]2)[CH2:14][C:15]([OH:17])=[O:16].S(=O)(=O)(O)O.[CH2:41](O)[CH3:42]>>[CH2:41]([O:17][C:15](=[O:16])[CH2:14][N:13]([CH2:12][C:11]([N:10]([N:2]1[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1]1)[CH3:35])=[O:34])[C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][C:26]=1[CH3:27])[NH:23][N:22]=[CH:21]2)[CH3:42]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 66881629HCID 66881629, compound

Product 1

HCID 66881861HCID 66881861, compoundYield 83%

Procedure

The compound (2.23 g, 4.67 mmol) of step A was dissolved in ethanol (60 ml), concentrated sulfuric acid (0.5 ml) was added at room temperature, and the mixture was heated under reflux for 80 min. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate. The organic layer was washed with aqueous sodium bicarbonate and saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure. The obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane) to give the title compound (1.64 g, yield 83%) as a colorless amorphous solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 80 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 aqueous sodium bicarbonate 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-a7de6bb8c7ce4e329871f86f78188d85
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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