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Triethylamine → Ethyl ((benzyloxy)carbonyl)-L-phenylalanylglycinate

HRID 1981930
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1981930
Cl.[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH2:7])[CH3:3].C(N(CC)CC)C.[C:16]([NH:26][C@H:27]([C:35](O)=[O:36])[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]>C(Cl)(Cl)Cl>[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH:7][C:35](=[O:36])[C@H:27]([CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[NH:26][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[CH3:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 2723640Glycine ethyl ester, hydrochloride

Produkt 1

HCID 12628842Ethyl ((benzyloxy)carbonyl)-L-phenylalanylglycinate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

Glycine ethyl ester.hydrochloride in an amount of 20.6 g was dissolved in 500 ml of chloroform and 20 ml of triethylamine was added thereto. Then, 57.2 g of carbobenzoxyphenylalanine p-nitorphenyl ester was added to the resulting mixture and the reaction was carried out overnight at room temperaure. The resulting mixture was washed with IN-NaHCO3, water, IN-HCl and water in this order and the chloroform layer was dried over magnesium sulfate MgSO4). After removing the solvent by distillation, the residue was recrystallized from ethyl acetate and petroleum ether to give carbobenzoxy-phenylalanyl-glycine ethyl ester having a melting point of 110°-112° C. in yield of 40.5 g (81%).

Aufarbeitung

  1. washThe resulting mixture was washed with IN-NaHCO3, water
  2. dry with materialIN-HCl and water in this order and the chloroform layer was dried over magnesium sulfate MgSO4)
  3. customAfter removing the solvent
  4. distillationby distillation
  5. customthe residue was recrystallized from ethyl acetate and petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-1bf0a74afba94c159cd08ef44754609a
Quelldatensatz
uspto-grants-1986_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04594409

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