3-Amino-5-chloro-2-hydroxybenzenesulfonic acid → N5-(2-hydroxy-3-sulfophenyl)-L-glutamine

HRID 1468309Notes

Reaction equation

HRID 1468309 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:8]([O:10]CC1C=CC=CC=1)=[O:9])[CH2:3][CH2:4][C:5](=O)[OH:6].C1N=CN(C(N2C=NC=C2)=O)C=1.[CH:40]1[C:45]([S:46]([OH:49])(=[O:48])=[O:47])=[C:44]([OH:50])[C:43]([NH2:51])=[CH:42][C:41]=1Cl.C1COCC1>C(Cl)Cl>[OH:50][C:44]1[C:45]([S:46]([OH:49])(=[O:48])=[O:47])=[CH:40][CH:41]=[CH:42][C:43]=1[NH:51][C:5](=[O:6])[CH2:4][CH2:3][C@@H:2]([C:8]([OH:10])=[O:9])[NH2:1]

Participants

6

Reactant 4

HCID 69273-Amino-5-chloro-2-hydroxybenzenesulfonic acidHCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 6994031(4S)-5-(Benzyloxy)-4-(((benzyloxy)carbonyl)amino)-5-oxopentanoic acid

Product 1

HCID 123937419N5-(2-hydroxy-3-sulfophenyl)-L-glutamineYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Z-Glu-OBn (371 mg, 1 mmol) was dissolved in methylene chloride (1 ml), and CDI (180 mg, 1.1 mmol) was added to the solution. The mixture was stirred at room temperature for 30 minutes. 2-Amino-4-chlorophenol-6-sulfonic acid (223 mg, 1 mmol) and THF (1 ml) were added to the mixture. The mixture was then stirred overnight at room temperature. After the solvent was removed by distillation, the mixture was purified in accordance with the purification step A. The resulting intermediate was dissolved in a methanol-water solvent mixture. A catalytic amount of Pd/C was added to the solution. The mixture was stirred overnight at room temperature in a hydrogen atmosphere. After the catalyst was filtered off, the solvent was removed by distillation. The mixture was purified according to the purification step A to give the title compound.

Workup

  1. stirringThe mixture was then stirred overnight at room temperature
  2. customAfter the solvent was removed by distillation
  3. customthe mixture was purified in accordance with the purification step A
  4. dissolutionThe resulting intermediate was dissolved in a methanol-water solvent mixture
  5. additionA catalytic amount of Pd/C was added to the solution
  6. stirringThe mixture was stirred overnight at room temperature in a hydrogen atmosphere
  7. filtrationAfter the catalyst was filtered off
  8. customthe solvent was removed by distillation
  9. customThe mixture was purified
  10. customaccording to the purification step A

Sources & evidence

ORD record
ord-35e8df3ff2784972ada939f7fbd69928
Source dataset
uspto-grants-2015_04
Patent number
US09000208B2

Reaction notes

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