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

HRID 705446Notes

Reaction equation

HRID 705446 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 thereto and stirred at room temperature for 30 minutes. Then, 2-amino-4-chlorophenol-6-sulfonic acid (223 mg, 1 mmol) and THF (1 mL) were added thereto and stirred overnight at room temperature. After removing a solvent, purification was conducted in accordance with the purification process A. The obtained intermediate was dissolved in a mixed solvent of methanol and water. Pd/C in catalyst quantity was added thereto and stirred under hydrogen atmosphere overnight at room temperature. After filtering out the catalyst and removing a solvent, purification was conducted in accordance with the purification process A to obtain a title compound.

Workup

  1. stirringstirred overnight at room temperature
  2. customAfter removing
  3. customa solvent, purification
  4. dissolutionThe obtained intermediate was dissolved in a mixed solvent of methanol and water
  5. additionPd/C in catalyst quantity was added
  6. stirringstirred under hydrogen atmosphere overnight at room temperature
  7. filtrationAfter filtering out the catalyst
  8. customremoving
  9. customa solvent, purification

Sources & evidence

ORD record
ord-9bfd7c16bd464110809a66a2efe0bc12
Source dataset
uspto-grants-2015_11
Patent number
US09174932B2

Reaction notes

Loading…