Hydrochloric Acid → HCID 19969538, compound

HRID 974856Notes

Reaction equation

HRID 974856 reaction equation
Cl.[OH:2][N:3]=[C:4]([CH2:19][CH:20]([CH3:22])[CH3:21])[C:5]([NH:7][CH:8]([C:14](OCC)=[O:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:6].CN(C)C.B>>[CH2:12]([O:11][C:9]([CH:8]1[NH:7][C:5](=[O:6])[CH:4]([CH2:19][CH:20]([CH3:22])[CH3:21])[N:3]([OH:2])[C:14]1=[O:15])=[O:10])[CH3:13]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 2723991N,N-Dimethylmethanamine--borane (1/1)HCID 86747153HCID 86747153, compound

Product 1

HCID 19969538HCID 19969538, compoundYield 18.6%

Procedure

240 ml of 7N hydrochloric acid (an ethanolic solution) was dropwise added to 240 ml of an ethanolic solution containing 18.46 g of diethyl N-(2-hydroxyimino-4-methylpentanoyl)aminomalonate and 5.49 g of borane-trimethylamine, with ice-cooling. The mixture was stirred at room temperature for 15 hours. The reaction mixture was subjected to vacuum distillation at room temperature to remove the solvent. The residue was dissolved in dichloromethane. The resulting solution was washed with an aqueous solution saturated with sodium chloride and an aqueous solution saturated with sodium hydrogen carbonate in this order, then dried with anhydrous magnesium sulfate, and was subjected to distillation to remove the solvent. The resulting yellow oily substance was dissolved in 120 ml of toluene. The solution was refluxed for 1 hour and then subjected to distillation to remove the solvent. 19.02 g of the resulting orange oily substance was purified by silica gel column chromatography (eluant: dichloromethane/methanol =30/1) to obtain 2.94 g of 3-ethoxycarbonyl-1-hydroxy-6-isobutylpiperazine-2,5-dione as an orange oily substance.

Workup

  1. temperaturewith ice-cooling
  2. distillationThe reaction mixture was subjected to vacuum distillation at room temperature
  3. customto remove the solvent
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washThe resulting solution was washed with an aqueous solution saturated with sodium chloride
  6. dry with materialan aqueous solution saturated with sodium hydrogen carbonate in this order, then dried with anhydrous magnesium sulfate
  7. distillationwas subjected to distillation
  8. customto remove the solvent
  9. dissolutionThe resulting yellow oily substance was dissolved in 120 ml of toluene
  10. temperatureThe solution was refluxed for 1 hour
  11. distillationsubjected to distillation
  12. customto remove the solvent
  13. custom19.02 g of the resulting orange oily substance was purified by silica gel column chromatography (eluant: dichloromethane/methanol =30/1)

Sources & evidence

ORD record
ord-853cb3f5ba3c414eb633f25a2c665213
Source dataset
uspto-grants-1997_03
Patent number
US05607934

Reaction notes

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