1,1'-Carbonyldiimidazole → N5-(4-hydroxy-3-sulfophenyl)-L-glutamine

HRID 1468310Notes

Reaction equation

HRID 1468310 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:8]([O:10]C(C)(C)C)=[O:9])[CH2:3][CH2:4][C:5](=[O:7])O.C1N=CN(C(N2C=NC=C2)=O)C=1.[NH2:34][C:35]1[CH:36]=[CH:37][C:38]([OH:45])=[C:39]([S:41]([O-:44])(=[O:43])=[O:42])[CH:40]=1.[Na+]>C(Cl)Cl.C1COCC1>[OH:45][C:38]1[CH:37]=[CH:36][C:35]([NH:34][C:5](=[O:7])[CH2:4][CH2:3][C@@H:2]([C:8]([OH:10])=[O:9])[NH2:1])=[CH:40][C:39]=1[S:41]([OH:44])(=[O:42])=[O:43]

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 6993444(4S)-5-(tert-butoxy)-4-{[(tert-butoxy)carbonyl]amino}-5-oxopentanoic acidHCID 89373065HCID 89373065, compound

Product 1

HCID 123936352N5-(4-hydroxy-3-sulfophenyl)-L-glutamine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Boc-Glu-OtBu (100 mg, 0.33 mmol) was dissolved in methylene chloride (1 ml) and THF (1 ml), and CDI (65 mg, 1.1 mmol) was added to the solution. The mixture was stirred for 30 minutes at room temperature. Sodium 5-amino-2-hydroxybenzenesulfonate (77 mg, 0.33 mmol) was added to the mixture and 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 2 ml of TFA. After stirring for 3 hours at room temperature, the solvent was distilled off. The mixture was purified according to the purification step A to give the title compound.

Workup

  1. stirringstirred 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 2 ml of TFA
  5. stirringAfter stirring for 3 hours at room temperature
  6. distillationthe solvent was distilled off
  7. customThe mixture was purified
  8. customaccording to the purification step A

Sources & evidence

ORD record
ord-da5ed68168a3467994faa085e668d03a
Source dataset
uspto-grants-2015_04
Patent number
US09000208B2

Reaction notes

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