Acetic Acid → N-(2-Cyanoethyl)-2-methylalanine

HRID 1042376Notes

Reaction equation

HRID 1042376 reaction equation
[CH3:1][C:2]([C:5]([OH:7])=[O:6])([CH3:4])[NH2:3].[OH-].[Na+].[C:10](#[N:13])[CH:11]=[CH2:12].C(O)(=O)C>O>[C:10]([CH2:11][CH2:12][NH:3][C:2]([CH3:4])([C:5]([OH:7])=[O:6])[CH3:1])#[N:13]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6119Aminoisobutyric acidHCID 7855AcrylonitrileHCID 14798Sodium Hydroxide

Product 1

HCID 13601735N-(2-Cyanoethyl)-2-methylalanineYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

50 g (0.48 mol) of 2-methylalanine were added to a cooled solution (water/ice) of NaOH (19.6 g) in water (100 ml). Once the solution had turned clear, 34 ml (0.50 mol) of acrylonitrile were dropped on cooling. The mixture was left overnight. After 18 hours, 28 ml of acetic acid were added on cooling (water/ice); a white solid precipitated; 200 ml of 95% ethanol were dropped in the flask, stirring was continued for 1 hour, then the mixture was allowed to stand in a fridge for 2-3 hours. After filtration, the solid was collected and dried in an oven at 80° C. The filtrates were evaporated and taken up with ethanol (160 ml). On cooling a further amount of product was obtained, which was filtered and dried. 72 g of the title compound were obtained from the first filtration. Total yield: 95%.

Workup

  1. temperatureon cooling
  2. waitAfter 18 hours
  3. customa white solid precipitated
  4. addition200 ml of 95% ethanol were dropped in the flask
  5. waitwas continued for 1 hour
  6. waitto stand in a fridge for 2-3 hours
  7. filtrationAfter filtration
  8. customthe solid was collected
  9. customdried in an oven at 80° C
  10. customThe filtrates were evaporated
  11. temperatureOn cooling a further amount of product
  12. customwas obtained
  13. filtrationwhich was filtered
  14. customdried

Sources & evidence

ORD record
ord-914ed0c89c1b4bb69cd4ab0df7d92988
Source dataset
uspto-grants-2013_10
Patent number
US08557845B2

Reaction notes

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