(2S)-2-aminobutyramide → (2S)-2-(4-methoxycarbonyl-2-oxo-1-pyrrolidinyl)butanamide

HRID 1866779Notes

Reaction equation

HRID 1866779 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6](O)O[C:8](=[O:10])[CH:9]=1)=[O:4].[NH2:12][C@@H:13]([CH2:17][CH3:18])[C:14]([NH2:16])=[O:15].[H][H]>CO.[Pd]>[NH2:16][C:14]([C@@H:13]([N:12]1[C:8](=[O:10])[CH2:9][CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6]1)[CH2:17][CH3:18])=[O:15]

Participants

6

Reactant 3

HCID 7015191(2S)-2-aminobutyramideHCID 13401719Methyl 2-hydroxy-5-oxo-2,5-dihydrofuran-3-carboxylateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 44367383(2S)-2-(4-methoxycarbonyl-2-oxo-1-pyrrolidinyl)butanamideYield 43%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

2-Hydroxy-5-oxo-2,5-dihydro-furan-3-carboxylic acid methyl ester (3.08 g) in methanol (40 ml) is added to a solution of (2S)-2-aminobutyramide (2.0 g) in methanol (30 ml) in a hydrogenation reactor and the mixture is maintained for at least 2 hours at room temperature. Then Pd/C catalyst (10 w/w %; Johnson Matthey 5% Pd on carbon—type 87L) is added and hydrogen introduced into the system under pressure. The temperature is kept at 40° C. maximum and the hydrogen pressure between 4 bar and 5 bar, followed by stirring for at least 20 hours following the initial reaction. The solution is then cooled between 15° C. and 25° C. and filtered to remove the catalyst. The solvent is evaporated under vacuum and the resulting yellow product is purified by preparative liquid chromatography (eluent: dichloromethane/methanol (95:5)) (Yield 43%).

Workup

  1. customis kept at 40° C.
  2. customreaction
  3. temperatureThe solution is then cooled between 15° C. and 25° C.
  4. filtrationfiltered
  5. customto remove the catalyst
  6. customThe solvent is evaporated under vacuum
  7. customthe resulting yellow product is purified by preparative liquid chromatography (eluent: dichloromethane/methanol (95:5)) (Yield 43%)

Sources & evidence

ORD record
ord-b172ff3323014caaa8b91c2c9769bc64
Source dataset
uspto-grants-2009_12
Patent number
US07629474B2

Reaction notes

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