HCID 178512946, compound → N-[(1S)-4-Amino-1-carboxybutyl]-D-glutamic acid

HRID 1090472Notes

Reaction equation

HRID 1090472 reaction equation
NC([NH:4][CH2:5][CH2:6][CH2:7][CH:8]([NH:12][CH:13]([CH2:17][CH2:18][C:19]([OH:21])=[O:20])[C:14]([OH:16])=[O:15])[C:9]([OH:11])=[O:10])=N>[OH-].[Na+]>[CH2:6]([CH2:5][NH2:4])[CH2:7][CH:8]([NH:12][CH:13]([C:14]([OH:16])=[O:15])[CH2:17][CH2:18][C:19]([OH:21])=[O:20])[C:9]([OH:11])=[O:10]

Participants

3

Reactant 1

HCID 178512946HCID 178512946, compound

Product 1

HCID 4474580N-[(1S)-4-Amino-1-carboxybutyl]-D-glutamic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
100 °C

Procedure

2 grams of nopaline were dissolved in 35 ml of 1M NaOH and the solution was heated at 100° C. for 12 hours. The reaction mixture was evaporated to dryness to remove ammonia and the crude solid material was dissolved in 25 ml of water. The pH was adjusted to 0.8 to 1.0 and the pH-adjusted solution was chromatographed on a strong cationic exchange column (H+ form). After washing with two column volumes of water, the column was eluted with 10% aqueous ammonia. The eluate containing the nopalinic acid was evaporated to dryness, dissolved in 15 ml of water, adjusted to pH 3.2-3.5 with 1M HCl, and recrystallized by adding approximately 1.5 volumes of ethanol (or acetone). The crystals were recrystallized from aqueous acetone. The characteristics of the compound were as follows:

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customto remove ammonia
  3. dissolutionthe crude solid material was dissolved in 25 ml of water
  4. customthe pH-adjusted solution was chromatographed on a strong cationic exchange column (H+ form)
  5. washAfter washing with two column volumes of water
  6. washthe column was eluted with 10% aqueous ammonia
  7. additionThe eluate containing the nopalinic acid
  8. customwas evaporated to dryness
  9. dissolutiondissolved in 15 ml of water
  10. customrecrystallized
  11. additionby adding approximately 1.5 volumes of ethanol (or acetone)
  12. customThe crystals were recrystallized from aqueous acetone

Sources & evidence

ORD record
ord-6c7e7bedc50d40929eb23185deb0f84c
Source dataset
uspto-grants-1992_01
Patent number
US05081289

Reaction notes

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