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Citric Acid → Cbz-Phe-NH-C2H4-NH-Boc

HRID 1157431
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1157431
[C:1]([NH:11][C@H:12]([C:20]([OH:22])=O)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].Cl.[C:24]([O:28][C:29]([NH:31][CH2:32][CH2:33][NH2:34])=[O:30])([CH3:27])([CH3:26])[CH3:25].O.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.C(N=C=NCCCN(C)C)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O.C(Cl)(Cl)Cl.CO>[NH:11]([C:1]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2])[C@H:12]([C:20]([NH:34][CH2:33][CH2:32][NH:31][C:29]([O:28][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:30])=[O:22])[CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

10

Edukt 6

HCID 311Citric AcidHCID 79724-MethylmorpholineHCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 187200tert-Butyl N-(2-aminoethyl)carbamate hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Produkt 1

HCID 20769586Cbz-Phe-NH-C2H4-NH-BocAusbeute 86,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 6212ChloroformLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

N-carbobenzoxy-L-phenylalanine (Cbz-Phe: 7.16 g, 25.4 mmol), N-t-butoxycarbonyl-ethylenediamine hydrochloride (5.00 g, 25.4 mmol), 1-hydroxybenzotriazole hydrate (HOBT: 4.28 g, 28.0 mmol), and N-methylmorpholine (NMM: 3.07 mL, 28.0 mmol) were dissolved in 100 mL of dimethylformamide (DMF), to which 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC: 5.36 g, 28.0 mmol) was then added under stirring and cooling with ice, followed by stirring at room temperature for one day. A 10% citric acid aqueous solution was added to the reaction solution, and the precipitated solid was dissolved in chloroform and a small amount of methanol, followed by washing the solution with a saturated sodium bicarbonate solution and a saturated saline solution before drying with sodium sulfate. It was concentrated under reduced pressure, followed by purifying the resultant residue using silica gel column chromatography (elution solvent: chloroform:methanol=95:5) to provide 9.69 g of the title compound as a white solid.

Aufarbeitung

  1. additionwas then added
  2. temperaturecooling with ice
  3. stirringby stirring at room temperature for one day
  4. washby washing the solution with a saturated sodium bicarbonate solution
  5. dry with materiala saturated saline solution before drying with sodium sulfate
  6. concentrationIt was concentrated under reduced pressure
  7. customby purifying the resultant residue
  8. washsilica gel column chromatography (elution solvent: chloroform:methanol=95:5)

Quellen und Nachweise

ORD-Eintrag
ord-469f863ad86c4482ac3e29f3c5affede
Quelldatensatz
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07807675B2

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