Ethanol → HCID 9928694, compound

HRID 349400Notes

Reaction equation

HRID 349400 reaction equation
[N:1]1([CH:6]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:24])[CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[CH:12][CH:11]=2)[CH:7]([CH3:9])[CH3:8])[CH:5]=[CH:4][N:3]=[CH:2]1.OS(O)(=O)=O.[CH2:30](O)[CH3:31]>>[N:1]1([CH:6]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:24])[CH2:18][CH2:19][CH2:20][C:21]([O:23][CH2:30][CH3:31])=[O:22])=[CH:12][CH:11]=2)[CH:7]([CH3:9])[CH3:8])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 22335517HCID 22335517, compound

Product 1

HCID 9928694HCID 9928694, compoundYield 18%

Procedure

A mixture of (compound 218) (0.023 mol) in ethanol (200 ml) and H2SO4 (3 ml) was stirred and refluxed for 12 hours. When the reaction was complete, the solvent was evaporated, the residue was taken up in water and extracted with CH2Cl2. The organic layer was dried, filtered and the solvent evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 97/3/0.1). The pure fractions were collected and evaporated. The residue was crystallized from 2-butanone and DIPE, yielding 1.45 g (18%) of (±)-ethyl 5-[[4-[1-(1H-imidazol-1-yl)-2-methylpropyl]phenyl]amino]-5-oxopentanoate (compound 219).

Workup

  1. temperaturerefluxed for 12 hours
  2. customthe solvent was evaporated
  3. extractionextracted with CH2Cl2
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. customthe solvent evaporated
  7. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 97/3/0.1)
  8. customThe pure fractions were collected
  9. customevaporated
  10. customThe residue was crystallized from 2-butanone and DIPE

Sources & evidence

ORD record
ord-6ea0386de2884979b6d71f0ea7edba00
Source dataset
uspto-grants-2007_02
Patent number
US07179825B2

Reaction notes

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