DL-Glutamic acid → HCID 12942451, compound

HRID 904177Notes

Reaction equation

HRID 904177 reaction equation
[CH2:1]([N:5]=[C:6]=[O:7])[CH2:2][CH2:3][CH3:4].[NH2:8][CH:9]([C:15](O)=[O:16])[CH2:10][CH2:11][C:12]([OH:14])=[O:13]>[OH-].[Na+]>[CH2:1]([N:5]1[C:15](=[O:16])[CH:9]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])[NH:8][C:6]1=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 611DL-Glutamic acidHCID 8110Butyl isocyanate

Product 1

HCID 12942451HCID 12942451, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

n-Butyl isocyanate (7.5 g, 0.075 mole) was added dropwise to a stirred solution of DL-glutamic acid (7.35 g, 0.05 mole) in aqueous sodium hydroxide (4.0 g, in 50 ml) at 0° C. The mixture was stirred at 0° C. for 2 hours then left to rise to room temperature overnight. The mixture was filtered and the filtrate acidified with concentrated hydrochloric acid (50 ml) and heated on a steam-bath for 30 minutes. The solution was cooled whence crystals separated which were collected at the pump and recrystallised from methanol to give prisms, m.p. 130.5° C. Yield 8.7 g=76%.

Workup

  1. waitthen left
  2. waitto rise to room temperature overnight
  3. filtrationThe mixture was filtered
  4. temperatureheated on a steam-bath for 30 minutes
  5. temperatureThe solution was cooled whence crystals
  6. customseparated which
  7. customwere collected at the pump
  8. customrecrystallised from methanol
  9. customto give prisms, m.p. 130.5° C

Sources & evidence

ORD record
ord-8b6dac5093a14d4e9474fc8f51c7f6c1
Source dataset
uspto-grants-1980_10
Patent number
US04230716

Reaction notes

Loading…