Hydrogen Bromide → HCID 9815549, compound

HRID 2300022Notes

Reaction equation

HRID 2300022 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×

Conditions

Temperature
40 °C

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 acetcnitrile 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. (See FIG. 1 for reaction Scheme.)

Workup

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

Sources & evidence

ORD record
ord-43d96c71422145fca2dffb16433657f3
Source dataset
uspto-grants-2002_12
Patent number
US06498150B2

Reaction notes

Loading…