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

HRID 330856Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 330856
[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]

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a88712e0e5be4788984548a6efc38299
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877739B2

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