Butyl (2E)-3-[2-{(2,2-dimethylpropanoyl)[(2-oxo-1,3-dioxolan-4-yl)methyl]amino}-6-(methyloxy)-3-pyridinyl]-2-propenoate → Butyl 3-[2-{(2,2-dimethylpropanoyl)[(2-oxo-1,3-dioxolan-4-yl)methyl]amino}-6-(methyloxy)-3-pyridinyl]propanoate

HRID 1943135Notes

Reaction equation

HRID 1943135 reaction equation
[CH3:1][C:2]([CH3:31])([CH3:30])[C:3]([N:5]([CH2:23][CH:24]1[CH2:28][O:27][C:26](=[O:29])[O:25]1)[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]>[CH3:30][C:2]([CH3:1])([CH3:31])[C:3]([N:5]([CH2:23][CH:24]1[CH2:28][O:27][C:26](=[O:29])[O:25]1)[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 86642090Butyl (2E)-3-[2-{(2,2-dimethylpropanoyl)[(2-oxo-1,3-dioxolan-4-yl)methyl]amino}-6-(methyloxy)-3-pyridinyl]-2-propenoateHCID 178418361HCID 178418361, compound

Product 1

HCID 68596362Butyl 3-[2-{(2,2-dimethylpropanoyl)[(2-oxo-1,3-dioxolan-4-yl)methyl]amino}-6-(methyloxy)-3-pyridinyl]propanoateYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of butyl (2E)-3-[2-{(2,2-dimethylpropanoyl)[(2-oxo-1,3-dioxolan-4-yl)methyl]amino}-6-(methyloxy)-3-pyridinyl]-2-propenoate (6.156 g, 14.184 mmol) in ethanol (200 ml) was treated with palladium on carbon (10% paste, 1.23 g) and the mixture was then stirred at rt under 1 atmosphere of hydrogen for 18 h. The reaction mixture was then filtered through a thin pad of Celite, eluting with more ethanol (200 ml). The organic filtrate was then evaporated to give the product as a yellow oil (6.065 g, 98%).

Workup

  1. filtrationThe reaction mixture was then filtered through a thin pad of Celite
  2. washeluting with more ethanol (200 ml)
  3. customThe organic filtrate was then evaporated

Sources & evidence

ORD record
ord-01723fc2ddca441090de6c48d00c30d3
Source dataset
uspto-grants-2013_03
Patent number
US08389524B2

Reaction notes

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