Butyl (2E)-3-[2-[(2,2-dimethylpropanoyl)amino]-6-(methyloxy)-3-pyridinyl]-2-propenoate → Butyl 3-[2-[(2,2-dimethylpropanoyl)amino]-6-(methyloxy)-3-pyridinyl]propanoate

HRID 420668Notes

Reaction equation

HRID 420668 reaction equation
[CH3:1][C:2]([CH3:24])([CH3:23])[C:3]([NH:5][C:6]1[C:11](/[CH:12]=[CH:13]/[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH3:20])=[O:15])=[CH:10][CH:9]=[C:8]([O:21][CH3:22])[N:7]=1)=[O:4].[H][H]>C(O)C.[Pd]>[CH3:23][C:2]([CH3:1])([CH3:24])[C:3]([NH:5][C:6]1[C:11]([CH2:12][CH2:13][C:14]([O:16][CH2:17][CH2:18][CH2:19][CH3:20])=[O:15])=[CH:10][CH:9]=[C:8]([O:21][CH3:22])[N:7]=1)=[O:4]

Participants

5

Reactant 2

HCID 58001729Butyl (2E)-3-[2-[(2,2-dimethylpropanoyl)amino]-6-(methyloxy)-3-pyridinyl]-2-propenoateHCID 178418361HCID 178418361, compound

Product 1

HCID 58001728Butyl 3-[2-[(2,2-dimethylpropanoyl)amino]-6-(methyloxy)-3-pyridinyl]propanoateYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of butyl (2E)-3-[2-[(2,2-dimethylpropanoyl)amino]-6-(methyloxy)-3-pyridinyl]-2-propenoate (43.706 g, 131 mmol) in ethanol (450 ml) under argon at rt was treated with palladium on carbon (10% paste) (5.0 g, 47.0 mmol) and then stirred at rt under 1 atmosphere of hydrogen for 90 h. The reaction mixture was then filtered through a thin pad of Kieselguhr, washing the product through with further ethanol (200 ml). The solvent was then evaporated to give product as a yellow solid (43.549 g, 99%).

Workup

  1. filtrationThe reaction mixture was then filtered through a thin pad of Kieselguhr
  2. washwashing the product through with further ethanol (200 ml)
  3. customThe solvent was then evaporated

Sources & evidence

ORD record
ord-cb6bfe2808f04642b5aaf37f230d9b93
Source dataset
uspto-grants-2012_01
Patent number
US08097628B2

Reaction notes

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