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

HRID 2402924Notes

Reaction equation

HRID 2402924 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-4274c1c2429b4fa28f6e6154dae395b4
Source dataset
uspto-grants-2014_08
Patent number
US08796485B2

Reaction notes

Loading…