Hydrogen Bromide → HCID 9815549, compound

HRID 1280828Notes

Reaction equation

HRID 1280828 reaction equation
C([NH:11][CH2:12][CH2:13][C:14]([NH:16][CH2:17][CH2:18][S:19]([OH:22])(=[O:21])=[O:20])=[O:15])(OCC1C=CC=CC=1)=O.Br>CC(O)=O>[NH2:11][CH2:12][CH2:13][C:14]([NH:16][CH2:17][CH2:18][S:19]([OH:22])(=[O:20])=[O:21])=[O:15]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 9927496Carbobenzoxy-beta-alanyltaurine

Product 1

HCID 9815549HCID 9815549, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

N-carbobenzoxy-β-alanyl-taurine (1.00 g, 3.4 mmol) was slurried in 23 ml glacial AcOH. To the mixture was added 3.4 mL HBr in AcOH (30 wt %) to result in a clear solution. The reaction was heated to 40/C and allowed to mix overnight. The product precipitated out of solution and acetonitrile was added to force the precipitation. The mixture was filtered, the filter cake washed and the product collected. The crude Br salt was loaded onto an ion exchange column (Dowex AG1-XB8). The column was eluted with H2O. The product cut was collected and lyophilized to give 583 mg of β-alanyl-taurine (87.3%). The zinc salt was prepared by treatment with Zn(OH)2 in H2O, followed by lyophilization.

Workup

  1. customto result in a clear solution
  2. temperatureThe reaction was heated to 40/C
  3. additionto mix overnight
  4. customThe product precipitated out of solution and acetonitrile
  5. additionwas added
  6. customthe precipitation
  7. filtrationThe mixture was filtered
  8. washthe filter cake washed
  9. customthe product collected
  10. washThe column was eluted with H2O
  11. customThe product cut was collected

Sources & evidence

ORD record
ord-464f9c334bb541b785e9a7e13a897376
Source dataset
uspto-grants-2002_09
Patent number
US06451853B1

Reaction notes

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