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

HRID 705447Notes

Reaction equation

HRID 705447 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]([OH:44])(=[O:43])=[O:42])[CH:40]=1>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 760765-Amino-2-hydroxybenzenesulphonic acidHCID 6993444(4S)-5-(tert-butoxy)-4-{[(tert-butoxy)carbonyl]amino}-5-oxopentanoic acid

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). CDI (65 mg, 1.1 mmol) was added thereto and stirred at room temperature for 30 minutes. Then, 5-amino-2-hydroxybenzene sulfonic acid salt (77 mg, 0.33 mmol) was 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 2 mL of TFA and stirred at room temperature for 3 hours, and a solvent was removed therefrom. The obtained product was purified 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 2 mL of TFA
  5. stirringstirred at room temperature for 3 hours
  6. customa solvent was removed
  7. customThe obtained product was purified in accordance with the purification process

Sources & evidence

ORD record
ord-8dcbabb5b1054d79917b06eb26747c46
Source dataset
uspto-grants-2015_11
Patent number
US09174932B2

Reaction notes

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