1-(Phenylmethyl) butanedioate → HCID 19815239, compound

HRID 466125Notes

Reaction equation

HRID 466125 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=1.[CH2:9]([O:16][C:17]([CH2:19][CH2:20][C:21](O)=[O:22])=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[CH2:9]([O:16][C:17]([CH2:19][CH2:20][C:21]([O:1][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=1)=[O:22])=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 87881-(Phenylmethyl) butanedioateHCID 10868DicyclohexylcarbodiimideHCID 546960044-Hydroxy-2(1H)-pyridinone

Product 1

HCID 19815239HCID 19815239, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.00 g of 4-hydroxy-2-pyridone and 2.00 g of 3-benzyloxycarbonylpropionic acid in 30 ml of dimethylformamide was added at room temperature 1.90 g of N,N'-dicyclohexylcarbodiimide with stirring and the mixture was stirred overnight. The crystals formed were filtered off and the filtrate was concentrated. The concentrate was dissolved in 50 ml of ethyl acetate and washed with 20 ml of water three times. The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated. The concentrate was then subjected to silica gel column chromatography using as an eluent 2% methanol-chloroform, giving 0.62 g of the title compound in a yield of 23%.

Workup

  1. stirringthe mixture was stirred overnight
  2. customThe crystals formed
  3. filtrationwere filtered off
  4. concentrationthe filtrate was concentrated
  5. dissolutionThe concentrate was dissolved in 50 ml of ethyl acetate
  6. washwashed with 20 ml of water three times
  7. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-be969529723b4b5080cb8a23be5a5615
Source dataset
uspto-grants-1992_10
Patent number
US05155113

Reaction notes

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