Tetrahydrofuran → Ethyl 3-{[(4-aminophenyl)carbonyl](methyl)amino}propanoate

HRID 1877279Notes

Reaction equation

HRID 1877279 reaction equation
[CH3:1][N:2]([C:10](=[O:20])[C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=1)[CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].O1CCCC1>[C].[Pd].C(O)C>[NH2:17][C:14]1[CH:13]=[CH:12][C:11]([C:10]([N:2]([CH3:1])[CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[O:20])=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 61794881Ethyl 3-[methyl(4-nitrobenzoyl)amino]propanoate

Product 1

HCID 46941342Ethyl 3-{[(4-aminophenyl)carbonyl](methyl)amino}propanoateYield 112%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of ethyl 3-[methyl(4-nitrobenzoyl)amino]propanoate (26.6 g) synthesized above, 5% palladium-carbon (8.9 g), tetrahydrofuran (150 mL) and ethanol (150 mL) was stirred at room temperature overnight under a hydrogen atmosphere. 5% palladium-carbon was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2, volume ratio) to give the title compound (26.6 g, 90%) as an oil.

Workup

  1. filtration5% palladium-carbon was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2, volume ratio)

Sources & evidence

ORD record
ord-78538291b8c54fa1a647cedd5bfc58d1
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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