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Dicyclohexylcarbodiimide → Z-Ser-NHNH-Boc

HRID 2119110
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2119110
[NH:1]([C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[C@H:2]([C:5]([OH:7])=O)[CH2:3][OH:4].[C:18]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])(=[O:21])[NH:19][NH2:20].C1C2C3C(=O)N(O)C(=O)C3C1C=C2.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C>[NH:1]([C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[C@H:2]([C:5]([NH:20][NH:19][C:18]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:7])[CH2:3][OH:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 70091tert-Butyl carbazateHCID 895293a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dioneHCID 100310N-(Benzyloxycarbonyl)-L-serine

Produkt 1

HCID 13469056Z-Ser-NHNH-Boc

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

Z-Ser-OH (10.0 g) and 6.2 g of t-butyl carbazate were dissolved in 150 ml of DMF and the solution was ice-cooled. HONB (8.0 g) and 9.3 g of DCC were added and the mixture was stirred for 15 hours. The formed DCU was filtered off and the filtrate was concentrated. The residue was extracted into AcOEt and the AcOEt solution was washed with 4% aqueous NaHCO3 and 10% aqueous citric acid, dried over Na2SO4 and concentrated. Ether was added and the crystals was collected by filtration. Yield 7.3 g (50.4%), mp 95°-98° C., [α]D26 -6.2° (c=0.8, DMF), Rf1 0.62.

Aufarbeitung

  1. temperaturecooled
  2. filtrationThe formed DCU was filtered off
  3. concentrationthe filtrate was concentrated
  4. extractionThe residue was extracted into AcOEt
  5. washthe AcOEt solution was washed with 4% aqueous NaHCO3 and 10% aqueous citric acid
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. additionEther was added
  9. filtrationthe crystals was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-80daa5f88ed14b4a94aff7fb10fdef83
Quelldatensatz
uspto-grants-1987_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04681848

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