1-Phenylpiperazine → 1-(N-Benzyloxycarbonyltyrosyl)-4-phenylpiperazine

HRID 5727

Reaktionsgleichung

Reaktionsgleichung von HRID 5727
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:21]([OH:23])=O)[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24]1([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:21]([N:33]1[CH2:34][CH2:35][N:30]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:31][CH2:32]1)=[O:23])[CH2:13][C:14]1[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 70961-PhenylpiperazineHCID 10868DicyclohexylcarbodiimideHCID 712438N-benzyloxycarbonyl-l-tyrosine

Produkt 1

HCID 544638561-(N-Benzyloxycarbonyltyrosyl)-4-phenylpiperazineAusbeute 58,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

12.3 g of N-benzyloxycarbonyltyrosine and 6.6 g of N-phenylpiperazine were dissolved in 150 ml of methylene chloride, and to the solution was added 8.4 g of DCC, and the mixture was stirred at a room temperature for 5 hours. Precipitated insoluble matter was filtered off and the filtrate was concentrated under a reduced pressure, and resulting residue was applied to a silica gel column and eluted with hexane/ethyl acetate (1:1 to 1:2) to obtain 10.5 g of the title compound in a colorless amorphous form.

Aufarbeitung

  1. filtrationPrecipitated insoluble matter was filtered off
  2. concentrationthe filtrate was concentrated under a reduced pressure
  3. customresulting residue
  4. washeluted with hexane/ethyl acetate (1:1 to 1:2)

Quellen und Nachweise

ORD-Eintrag
ord-6fb0cb4113fb499eb4dfc30867774f34
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05245034

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