Pyruvic Acid → HCID 13405026, compound

HRID 1049574Notes

Reaction equation

HRID 1049574 reaction equation
C(Cl)(=O)C(Cl)=O.[C:7]([OH:12])(=O)[C:8]([CH3:10])=[O:9].CN(C=O)C.[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1>C1COCC1>[O:21]1[CH2:22][CH2:23][N:18]([C:7](=[O:12])[C:8](=[O:9])[CH3:10])[CH2:19][CH2:20]1

Participants

6

Reactant 4

HCID 1060Pyruvic AcidHCID 6228DimethylformamideHCID 8083MorpholineHCID 65578Oxalyl chloride

Product 1

HCID 13405026HCID 13405026, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, oxalyl chloride (8.75 mL) was added to a solution of pyruvic acid (6.96 mL) and DMF (77 μL) in THF (200 mL) at room temperature, and the mixture was stirred at room temperature for 20 min. Under a nitrogen atmosphere, morpholine (18.4 mL) was added to the reaction mixture at 0° C., and the mixture was stirred at room temperature for 2 hr. The reaction mixture was filtered, the solvent of the filtrate was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (11.0 g) as a colorless oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hr
  2. filtrationThe reaction mixture was filtered
  3. customthe solvent of the filtrate was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a5cdae9346124d2baba651c319a4b68e
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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