(E)-3-dipropylcarbamoyl-2-methylacrylic acid → N,N-dipropyl 2-methylsuccinamic acid

HRID 20448Notes

Reaction equation

HRID 20448 reaction equation
[CH2:1]([N:4]([CH2:13][CH2:14][CH3:15])[C:5](/[CH:7]=[C:8](\[CH3:12])/[C:9]([OH:11])=[O:10])=[O:6])[CH2:2][CH3:3]>[Pd].O1CCCC1>[CH2:13]([N:4]([CH2:1][CH2:2][CH3:3])[C:5](=[O:6])[CH2:7][CH:8]([CH3:12])[C:9]([OH:11])=[O:10])[CH2:14][CH3:15]

Participants

4

Reactant 1

HCID 86615362(E)-3-dipropylcarbamoyl-2-methylacrylic acid

Product 1

HCID 86236677N,N-dipropyl 2-methylsuccinamic acidYield 66.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Add 40% palladium on carbon (0.064 g) to a solution of (E)-3-dipropylcarbamoyl-2-methylacrylic acid (0.20 g, 0.94 mmol) in tetrahydrofuran (20 mL). Hydrogenate at 60 psi for 18 hours. Filter through a filtering agent and concentrate filtrate under reduced pressure. Subject residue to silica gel chromatography, eluting with dichloromethane containing 10-40% of 5% (2:1 methanol:acetic acid) in dichloromethane to provide the title compound (0.134 g, 66.4%).

Workup

  1. filtrationFilter through a filtering agent
  2. concentrationconcentrate filtrate under reduced pressure
  3. washSubject residue to silica gel chromatography, eluting with dichloromethane containing 10-40% of 5% (2:1 methanol:acetic acid) in dichloromethane

Sources & evidence

ORD record
ord-6ac1697f97b645e397a63d1779cdab26
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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