Morpholine → Z-(L)-Tyr morpholin-4-ylamide

HRID 263762

Reaktionsgleichung

Reaktionsgleichung von HRID 263762
C1CCC(N=C=NC2CCCCC2)CC1.[NH:16]([C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30])[C@H:17]([C:26]([OH:28])=[O:27])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1.C1C=CC2N(O)[N:46]=[N:45][C:43]=2[CH:44]=1.N1CC[O:52][CH2:51][CH2:50]1>C(Cl)Cl>[NH:16]([C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30])[C@H:17]([C:26]([OH:28])=[O:27])[CH2:18][C:19]1[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=1.[N:45]1([NH-:46])[CH2:43][CH2:44][O:52][CH2:51][CH2:50]1

Komponenten

6

Edukt 4

HCID 8083MorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 712438N-benzyloxycarbonyl-l-tyrosine

Produkt 1

HCID 131720080Z-(L)-Tyr morpholin-4-ylamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

9.08 g (44 mmol) of DCC are added to an ice-cooled suspension of 14.04 g (40 mmol) of Z-(L)-Tyr-OH in 750 ml of methylene chloride and the mixture is stirred for 20 min. Subsequently, 10.81 g (80 mmol) of HOBT and a solution of 5.23 g (60 mmol) of morpholine in 50 ml of methylene chloride are added. The mixture is stirred for 18 h at RT and then filtered. The filtrate is washed with sat. NaHCO3 solution, water and brine and the aqueous phases are extracted with 2 portions of methylene chloride. The organic phases are dried with Na2SO4, concentrated by evaporation and subjected to column chromatography (SiO2, ethyl acetate) to yield the title compound: TLC Rf (B)=0.39.

Aufarbeitung

  1. temperaturecooled
  2. stirringThe mixture is stirred for 18 h at RT
  3. filtrationfiltered
  4. washThe filtrate is washed with sat. NaHCO3 solution, water and brine
  5. extractionthe aqueous phases are extracted with 2 portions of methylene chloride
  6. dry with materialThe organic phases are dried with Na2SO4
  7. concentrationconcentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-7a48c605085c4128acc0de33eaee2cb8
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05643878

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