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Ethylmorpholine → Z-Tyr(But)-Gly-OEt

HRID 1154150
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1154150
C(N1CCOCC1)C.C1CCC(N=C=NC2CCCCC2)CC1.[NH:24]([C:41]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:42])[C@H:25]([C:38](O)=[O:39])[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:29][CH:28]=1.[NH2:51][CH2:52][C:53]([O:55][CH2:56][CH3:57])=[O:54].Cl.C1C=CC2N(O)N=NC=2C=1>CN(C)C=O>[NH:24]([C:41]([O:43][CH2:44][C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)=[O:42])[C@H:25]([C:38]([NH:51][CH2:52][C:53]([O:55][CH2:56][CH3:57])=[O:54])=[O:39])[CH2:26][C:27]1[CH:28]=[CH:29][C:30]([O:33][C:34]([CH3:35])([CH3:37])[CH3:36])=[CH:31][CH:32]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 978520O-(1,1-Dimethylethyl)-N-((phenylmethoxy)carbonyl)-L-tyrosineHCID 2723640Glycine ethyl ester, hydrochloride

Produkt 1

HCID 13178769Z-Tyr(But)-Gly-OEt

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

6.4 ml (50 mmoles) of N-ethylmorpholine and 11.33 g (55 mmoles) of DCC are added at 0° C. and while stirring to a solution of 18.55 g (50 mmoles) of Z-Tyr(But)-OH, 6.98 g (50 mmoles) of H-Gly-OEt.HCl and 6.75 g (50 mmoles) of HOBt in 75 ml of dimethylformamide. The mixture is stirred for 2 hours at 0° C. and is allowed to stand overnight at room temperature. The precipitate is filtered off and the filtrate is concentrated in a high vacuum. The residue is partitioned between ethyl acetate and water. The ethyl acetate phase is extracted by shaking with NaHCO3 solution, a KHSO4 /K2SO4 buffer and water, and is dried over Na2SO4 and concentrated. The residue is dissolved in diisopropyl ether. Undissolved material is filtered off and petroleum ether is added to the filtrate. The mixture is cooled for a few hours in an ice bath and the precipitate is filtered off. Yield 20.63 g (89%), melting point 108° C. [α]D22 =-13.4° (c=1, methanol).

Aufarbeitung

  1. waitto stand overnight at room temperature
  2. filtrationThe precipitate is filtered off
  3. concentrationthe filtrate is concentrated in a high vacuum
  4. customThe residue is partitioned between ethyl acetate and water
  5. extractionThe ethyl acetate phase is extracted
  6. stirringby shaking with NaHCO3 solution
  7. dry with materiala KHSO4 /K2SO4 buffer and water, and is dried over Na2SO4
  8. concentrationconcentrated
  9. dissolutionThe residue is dissolved in diisopropyl ether
  10. filtrationUndissolved material is filtered off
  11. additionpetroleum ether is added to the filtrate
  12. temperatureThe mixture is cooled for a few hours in an ice bath
  13. filtrationthe precipitate is filtered off
  14. customYield 20.63 g (89%), melting point 108° C. [α]D22 =-13.4° (c=1, methanol)

Quellen und Nachweise

ORD-Eintrag
ord-d695d153319a43da9eba32413d7b1a09
Quelldatensatz
uspto-grants-1984_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04487764

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