Pyruvic Acid → HCID 53755695, compound

HRID 35176

Reaction equation

HRID 35176 reaction equation
[C:1]([OH:6])(=O)[C:2]([CH3:4])=[O:3].[CH2:7]([O:9][C:10](=[O:16])[C@@H:11]1[CH2:15][CH2:14][CH2:13][NH:12]1)[CH3:8].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)(Cl)Cl>[CH2:7]([O:9][C:10](=[O:16])[C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:1](=[O:6])[C:2]([CH3:4])=[O:3])[CH3:8]

Participants

5

Reactant 3

HCID 1060Pyruvic AcidHCID 10868DicyclohexylcarbodiimideHCID 79888L-Proline, ethyl ester

Product 1

HCID 53755695HCID 53755695, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
-5 °C

Procedure

A solution of 60 mmoles of pyruvic acid plus 60 mmoles of L-proline ethyl ester in redistilled chloroform is cooled to -50° C. in an acetone-dry ice bath. To this solution is added 60 mmoles of a precooled solution of dicyclohexylcarbodiimide (DCC) in cloroform and the mixture is stirred at -5° C. for 1 hour. The reaction mixture is slowly warmed to room temperature and stirred for an additional 2 hours and then stirred at 4° C. overnight. The mixture is filtered to remove dicyclohexylurea, then cooled in an ice bath. The organic phase is washed with cold water, cold 1N NaHCO3 and finally with cold saturated NaCl. The organic phase is dried over anhydrous MgSO4 and filtered. The solvent is removed with a rotary evaporator yielding N-pyruvoyl-L-proline ethyl ester.

Workup

  1. temperatureThe reaction mixture is slowly warmed to room temperature
  2. stirringstirred for an additional 2 hours
  3. stirringstirred at 4° C. overnight
  4. filtrationThe mixture is filtered
  5. customto remove dicyclohexylurea
  6. temperaturecooled in an ice bath
  7. washThe organic phase is washed with cold water, cold 1N NaHCO3 and finally with cold saturated NaCl
  8. dry with materialThe organic phase is dried over anhydrous MgSO4
  9. filtrationfiltered
  10. customThe solvent is removed with a rotary evaporator

Sources & evidence

ORD record
ord-8c36c7ea9bdf4d7584a59061c541e8aa
Source dataset
uspto-grants-1988_08
Patent number
US04766110

Linked notes

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