Ethanol → HCID 59773581, compound

HRID 2220735Notes

Reaction equation

HRID 2220735 reaction equation
[C:1]([C:3]([CH3:11])=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[O-])#[N:2].[K+].CCO.Cl.[C:17]([NH:21][NH2:22])([CH3:20])([CH3:19])[CH3:18]>CCOC(C)=O.O>[CH2:9]([O:8][C:6]([C:4]1[C:3]([CH3:11])=[C:1]([NH2:2])[N:21]([C:17]([CH3:20])([CH3:19])[CH3:18])[N:22]=1)=[O:7])[CH3:10]

Participants

6

Reactant 3

HCID 702EthanolHCID 81889tert-Butylhydrazine monohydrochlorideHCID 74326182HCID 74326182, compound

Product 1

HCID 59773581HCID 59773581, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Placed 47 (1.0 eq.) into a sealed pressure reaction flask. Added EtOH and t-butylhydrazine hydrochloride (1.1 eq.). The pressure flask was capped and heated to reflux. After a time sufficient for reaction completion, the mixture was evaporated to dryness and the solid obtained was dissolved in equal amounts of EtOAc and water. The organic layer was washed with saturated aqueous NaHCO3, brine, dried with MgSO4, and evaporated. This slightly yellow solid was triturated with hexanes and filtered to afford ester 48.

Workup

  1. custominto a sealed pressure reaction flask
  2. customThe pressure flask was capped
  3. temperatureheated to reflux
  4. customAfter a time sufficient for reaction completion
  5. customthe mixture was evaporated to dryness
  6. customthe solid obtained
  7. washThe organic layer was washed with saturated aqueous NaHCO3, brine
  8. dry with materialdried with MgSO4
  9. customevaporated
  10. customThis slightly yellow solid was triturated with hexanes
  11. filtrationfiltered

Sources & evidence

ORD record
ord-8e3745037af34fbf8c350222c2b54686
Source dataset
uspto-grants-2008_08
Patent number
US07417152B2

Reaction notes

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