L-Alanine → (2S)-2-[[(2S)-1-ethoxy-1-oxopentan-2-yl]amino]propanoic acid

HRID 1835964Notes

Reaction equation

HRID 1835964 reaction equation
[NH2:1][C@H:2]([C:4]([OH:6])=[O:5])[CH3:3].[OH-].[Na+].O=[C:10]([CH2:16][CH2:17][CH3:18])[C:11]([O:13][CH2:14][CH3:15])=[O:12]>O.[Pd]>[CH3:18][CH2:17][CH2:16][C@H:10]([NH:1][C@H:2]([C:4]([OH:6])=[O:5])[CH3:3])[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

6

Reactant 3

HCID 5950L-AlanineHCID 14798Sodium HydroxideHCID 123521Ethyl 2-oxovalerate

Product 1

HCID 10015159(2S)-2-[[(2S)-1-ethoxy-1-oxopentan-2-yl]amino]propanoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent2×

Procedure

Into a tank, fitted with a stirrer, introduce 25 kg of L-alanine dissolved in water, 1.1 kg of sodium hydroxide and 36 kg of ethyl 2-oxopentanoate. Stir the reaction mixture for 30 minutes. Into a hydrogenation apparatus introduce 5% palladium-on-carbon suspended in water, then the mixture obtained above. Hydrogenate at ambient temperature at a pressure of 1 bar until the theoretical amount of hydrogen has been absorbed. Remove the catalyst by filtration, then add concentrated hydrochloric acid to the filtrate until a pH of 3 is obtained. Harvest the resulting solid by means of filtration, take up the cake in acetonitrile at reflux, filter while hot and then allow to crystallize.

Workup

  1. customInto a tank, fitted with a stirrer
  2. customthe mixture obtained above
  3. customHydrogenate at ambient temperature at a pressure of 1 bar until the theoretical amount of hydrogen has been absorbed
  4. customRemove the catalyst
  5. filtrationby filtration
  6. additionadd concentrated hydrochloric acid to the filtrate until a pH of 3
  7. customis obtained
  8. filtrationHarvest the resulting solid by means of filtration
  9. temperatureat reflux
  10. filtrationfilter while hot and
  11. customto crystallize

Sources & evidence

ORD record
ord-dbe8055aa0224967b912897500c26768
Source dataset
uspto-grants-2004_08
Patent number
US06774259B2

Reaction notes

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