Water → HCID 86751244, compound

HRID 1378307Notes

Reaction equation

HRID 1378307 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4]([OH:6])=[O:5].[NH2:10][C@H:11]([C:17]([OH:19])=[O:18])[CH2:12][CH2:13][C:14]([OH:16])=[O:15].O.C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:28][CH:29]([OH:32])[CH2:30]Br>[OH-].[Na+].C(O)C>[NH2:10][C@H:11]([C:17]([OH:19])=[O:18])[CH2:12][CH2:13][C:14]([OH:16])=[O:15].[NH2:1][C@@H:2]1[C:7](=[O:9])[O:8][CH2:28][C:29]([OH:32])([CH3:30])[O:6][C:4](=[O:5])[CH2:3]1

Participants

8

Reactant 5

HCID 962WaterHCID 5960L-Aspartic AcidHCID 72871,3-Dibromo-2-propanol2×HCID 10340Sodium CarbonateHCID 33032L-Glutamic Acid

Product 1

HCID 86751244HCID 86751244, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

8.5 g (0.064 mol) of L-aspartic acid and 9.4 g (0.0641 mol) L-glutamic acid is dissolved in 160 ml of water containing 10.2 g (0.255 mol) of sodium hydroxide. After dissolution, 6.8 g (0.064) sodium carbonate is added, followed by 80 ml ethanol. While refluxing the solution, 16.8 g (0.077 mol) 1,3-dibromo-2-propanol is added gradually during a period of 4 hours, followed by refluxing overnight. An additional 16.8 g (0.077 mol) of 1,3-dibromo-2-propanol is added, followed by all-day reflux. The solution is distilled to remove solvents and the resulting solid which contains HPAC and other materials is recovered and triturated with methanol/water. The purified solid is triturated again with methanol only and stirred overnight to remove residual materials, followed by dissolution in 10 cc water. Adjustment of the solution pH to 3-5 precipitates out HPAG. The final product is further purified by high pressure liquid chromotography.

Workup

  1. additionis added
  2. additionis added gradually during a period of 4 hours
  3. temperatureby refluxing overnight
  4. waitfollowed by all-day
  5. temperaturereflux
  6. distillationThe solution is distilled
  7. customto remove solvents
  8. customis recovered
  9. customtriturated with methanol/water
  10. customThe purified solid is triturated again with methanol only
  11. customto remove residual materials
  12. dissolutionfollowed by dissolution in 10 cc water
  13. customAdjustment of the solution pH to 3-5 precipitates out HPAG
  14. customThe final product is further purified by high pressure liquid chromotography

Sources & evidence

ORD record
ord-8f65f35bff7a45df8f5a553451b57bf5
Source dataset
uspto-grants-1997_09
Patent number
US05668098

Reaction notes

Loading…