Acetone → 10552-79-1

HRID 1107378Notes

Reaction equation

HRID 1107378 reaction equation
[ClH:1].[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH2:6].[CH3:8][C:9]([CH3:11])=O.[OH-].[Na+]>CO.[Pd]>[ClH:1].[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH:6][CH:9]([CH3:11])[CH3:8]

Participants

6

Reactant 3

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 122755Glycine methyl ester hydrochloride

Product 1

HCID 8669625110552-79-1Yield 19.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Part A: A mixture of glycine methyl ester hydrochloride (3.83 g, 30.5 mmol), acetone (1.77 g, 30.5 mmol) and NaOH (1.22 g, 30.5 mmol) in MeOH (200 mL) was stirred under an atmosphere of hydrogen (1 atm) in the presence of palladium on carbon (10%, 0.4 g) for 24 hours. The reaction was flushed with nitrogen and filtered through a Celite pad, acidified with HCl (1N), dried (MgSO4) and evaporated. Trituration of the residue with Et2O gave N-2-propylglycine methyl ester hydrochloride (1.0 g) as an off-white solid; LRMS (M+H)+ =132.1.

Workup

  1. customThe reaction was flushed with nitrogen
  2. filtrationfiltered through a Celite pad
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-99f47b7a6c2146e1925eb579793ac900
Source dataset
uspto-grants-2000_05
Patent number
US06060462

Reaction notes

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