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

HRID 2217347Notes

Reaction equation

HRID 2217347 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-methylalanine

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 mire 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).

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

Sources & evidence

ORD record
ord-5ca0bddf29bc494d82caae62f7479b7f
Source dataset
uspto-grants-2008_08
Patent number
US07407971B2

Reaction notes

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