(+-)-Aspartic Acid → HCID 12942452, compound

HRID 904178Notes

Reaction equation

HRID 904178 reaction equation
[NH2:1][CH:2]([C:7]([OH:9])=O)[CH2:3][C:4]([OH:6])=[O:5].[OH-].[Na+].[CH2:12]([N:16]=[C:17]=[O:18])[CH2:13][CH2:14][CH3:15]>>[CH2:12]([N:16]1[C:7](=[O:9])[CH:2]([CH2:3][C:4]([OH:6])=[O:5])[NH:1][C:17]1=[O:18])[CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 3

HCID 424(+-)-Aspartic AcidHCID 8110Butyl isocyanateHCID 14798Sodium Hydroxide

Product 1

HCID 12942452HCID 12942452, compound

Procedure

DL-Aspartic acid (6.65 g, 0.05 mole) in 2N-NaOH (50 ml, 2 equiv.) was cooled to 0° C. and n-butyl isocyanate (7.5 g, 0.075 mole) added during 15 minutes to the stirred solution. Stirring was continued for 2 hours and the mixture left at room temperature overnight. The mixture was then filtered, acidified with concentrated hydrochloric acid (50 ml) and heated on a steam-bath for 30 minutes. The mixture was cooled, diluted with water and continuously extracted with ether for 21/2 hours. Removal of the ether gave a solid which was recrystallised from ether to yield the product as prisms, m.p. 132° C. Yield 8.8 g=82%.

Workup

  1. waitthe mixture left at room temperature overnight
  2. filtrationThe mixture was then filtered
  3. temperatureheated on a steam-bath for 30 minutes
  4. temperatureThe mixture was cooled
  5. additiondiluted with water
  6. extractioncontinuously extracted with ether for 21/2 hours
  7. customRemoval of the ether
  8. customgave a solid which
  9. customwas recrystallised from ether

Sources & evidence

ORD record
ord-e7c01db9303040c0b9fca4082f8ec772
Source dataset
uspto-grants-1980_10
Patent number
US04230716

Reaction notes

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