Dicyclohexylcarbodiimide → Ethyl β-oxo-3-pyridinepentanoate

HRID 458443Notes

Reaction equation

HRID 458443 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][C:9]([OH:11])=O)[CH:2]=1.[CH3:12][C:13]1(C)[O:20]C(=O)[CH2:17][C:15](=O)[O:14]1.CN(C1C=CC=CN=1)C.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[O:11]=[C:9]([CH2:8][CH2:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[CH2:12][C:13]([O:14][CH2:15][CH3:17])=[O:20]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 218852-DimethylaminopyridineHCID 2596243-(Pyridin-3-yl)propanoic acid

Product 1

HCID 18441996Ethyl β-oxo-3-pyridinepentanoateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3-(3-pyridyl)propionic acid (13.6 g, 0.09 mol), Meldrum's acid (13.0 g, 0.09 mol) and dimethylaminopyridine (11 g, 0.09 mol) was added 1,3-dicyclohexylcarbodiimide (18.54 g, 0.09 mol) and DCM (140 ml). The reaction was stirred for 4 h, filtered, concentrated, diluted with 200 ml ethanol and 25 ml 4M HCl/dioxane. The mixture was warmed to reflux 2 h, concentrated, combined with excess sodium carbonate, followed by 50% sodium hydroxide, then triturated with ethyl acetate, filtered, dried (Na2SO4), filtered, then concentrated to give A as an amber oil (19.8 g, 100%). LCMS m/z 222 (MH+)

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. additiondiluted with 200 ml ethanol and 25 ml 4M HCl/dioxane
  4. temperatureThe mixture was warmed
  5. temperatureto reflux 2 h
  6. concentrationconcentrated
  7. customtriturated with ethyl acetate
  8. filtrationfiltered
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-b15cde4615004a5fae6422afa570492d
Source dataset
uspto-grants-2007_03
Patent number
US07189851B2

Reaction notes

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