Triethylamine → N-(t-butyloxycarbonyl)-4-benzyloxy-L-phenylalanine 3-pyridylamide

HRID 330423

Reaktionsgleichung

Reaktionsgleichung von HRID 330423
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:25](O)=[O:26])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C(Cl)(=O)OCC.[NH2:41][C:42]1[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=1>O1CCCC1>[N:44]1[CH:45]=[CH:46][CH:47]=[C:42]([NH:41][C:25](=[O:26])[C@H:9]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:15][CH:16]=2)[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH:43]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 100093-AminopyridineHCID 10928Ethyl chloroformateHCID 98763O-benzyl-N-((tert-butoxy)carbonyl)-L-tyrosine

Produkt 1

HCID 54368616N-(t-butyloxycarbonyl)-4-benzyloxy-L-phenylalanine 3-pyridylamideAusbeute 22,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

N-(t-butyloxycarbonyl)-4-benzyloxy-L-phenylalanine (I) (3.71 g) was dissolved in dry tetrahydrofuran (100 ml) and, under ice cooling, triethylamine (1.5 ml) was added thereto. After stirring for 15 minutes, ethyl chlorocarbonate (1.10 g) was added, followed by stirring for 30 minutes. To this solution was added 3-aminopyridine (0.94 g) and the reaction was carried out at room temperature for 7 hours. The solid was filtered off and the filtrate was concentrated under reduced pressure. The residue was extracted with ethyl acetate. After a conventional post-treatment, N-(t-butyloxycarbonyl)-4-benzyloxy-L-phenylalanine 3-pyridylamide (II) (1.01 g) was obtained.

Aufarbeitung

  1. stirringby stirring for 30 minutes
  2. waitthe reaction was carried out at room temperature for 7 hours
  3. filtrationThe solid was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. extractionThe residue was extracted with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-7ef08bdefa5e47119bc105eb466ad06b
Quelldatensatz
uspto-grants-1990_01
Patentnummer
US04895842

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