Benzaldehyde → HCID 9794172, compound

HRID 2226087Notes

Reaction equation

HRID 2226087 reaction equation
[OH-].[Na+].[NH2:3][CH:4]([C:6]([OH:8])=[O:7])[CH3:5].[CH:9](=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl>O>[NH2:3][C:4]([CH3:5])([CH:9]([OH:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:6]([OH:8])=[O:7]

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 602DL-alanineHCID 14798Sodium Hydroxide

Product 1

HCID 9794172HCID 9794172, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

Sodium hydroxide (6 g, 150 mmoles) and 8.9 g (100 mmoles) of D,L-alanine are dissolved in 25 mL of water and the solution cooled to around 5° C. while stirring under a nitrogen atmosphere. To the solution is added 21.2 g (200 mmoles) benzaldehyde and the mixture stirred at 5° C. for approximately one hour. The mixture is then warmed to room temperature and maintained for approximately 20 hours. Concentrated hydrochloric acid then is added to bring the reaction mixture to pH 2.0. After stirring the acidic solution for two hours, the aqueous phase is separated, extracted with ethyl acetate and evaporated under vacuum. The resulting material is twice extracted with 80 mL hot absolute ethanol, followed by evaporation of the ethanol. The resulting material is again extracted with 40 mL of absolute ethanol, followed by removal of the ethanol. The extract then is dissolved in at least a 1:1 methanol water solution and absorbed on polymethacrylate column. The column then is eluted with the same 1:1 methanol water solution and the 30 mL fractions are combined and evaporated. Purification on the polymethacrylate column then is repeated using 95% ethanol to yield racemic 2-amino-2-methyl-3-hydroxy-3-phenylpropionic acid.

Workup

  1. stirringthe mixture stirred at 5° C. for approximately one hour
  2. temperatureThe mixture is then warmed to room temperature
  3. temperaturemaintained for approximately 20 hours
  4. stirringAfter stirring the acidic solution for two hours
  5. customthe aqueous phase is separated
  6. extractionextracted with ethyl acetate
  7. customevaporated under vacuum
  8. extractionThe resulting material is twice extracted with 80 mL hot absolute ethanol
  9. customfollowed by evaporation of the ethanol
  10. extractionThe resulting material is again extracted with 40 mL of absolute ethanol
  11. customfollowed by removal of the ethanol
  12. extractionThe extract
  13. dissolutionthen is dissolved in at least a 1:1 methanol water solution
  14. customabsorbed on polymethacrylate column
  15. washThe column then is eluted with the same 1:1 methanol water solution
  16. customevaporated
  17. customPurification on the polymethacrylate column

Sources & evidence

ORD record
ord-198a87b0db0c4f8088d6115dbc0bc645
Source dataset
uspto-grants-1994_09
Patent number
US05346828

Reaction notes

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