Dicyclohexylcarbodiimide → 1-Benzyloxycarbonyl-4-(N-tert-butoxycarbonyltyrosyl)homopiperazine

HRID 5730

Reaktionsgleichung

Reaktionsgleichung von HRID 5730
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:18]([OH:20])=O)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:21]([O:28][C:29]([N:31]1[CH2:37][CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O.ON1C2C=CC=CC=2N=N1.C1CCC(N=C=NC2CCCCC2)CC1>O1CCCC1>[CH2:21]([O:28][C:29]([N:31]1[CH2:37][CH2:36][CH2:35][N:34]([C:18](=[O:20])[C@H:9]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=2)[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:33][CH2:32]1)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

6

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 117439L-Tyrosine, N-(1,1-dimethylethoxy)carbonyl-HCID 27960291-Hydroxybenzotriazole hydrateHCID 4384955Benzyl 1,4-diazepane-1-carboxylate

Produkt 1

HCID 540599341-Benzyloxycarbonyl-4-(N-tert-butoxycarbonyltyrosyl)homopiperazineAusbeute 97,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

15.29 g of N-tert-butoxycarbonyltyrosine and 12.73 g of N-benzyloxycarbonylhomopiperazine were dissolved in 280 ml of tetrahydrofuran, to the solution were added 8.09 g of 1-hydroxybenzotriazole hydrate and 11.77 g of DCC at a room temperature with stirring, and the reaction mixture was stirred for 16 hours. The reaction mixture was evaporated to remove the solvent under a reduced pressure, to the residue was added benzene, and insoluble matter was filtered by suction and washed with benzene. The benzene layers were combined and evaporated off under a reduced pressure. The resulting residue was applied to a silica gel column and eluted with chloroform/methanol (100:1), to obtain 26.42 g of the title compound in colorless amorphous form.

Aufarbeitung

  1. stirringthe reaction mixture was stirred for 16 hours
  2. customThe reaction mixture was evaporated
  3. customto remove the solvent under a reduced pressure
  4. additionto the residue was added benzene, and insoluble matter
  5. filtrationwas filtered by suction
  6. washwashed with benzene
  7. customevaporated off under a reduced pressure
  8. washeluted with chloroform/methanol (100:1)

Quellen und Nachweise

ORD-Eintrag
ord-5e959f0c247e4beda9969377311282aa
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05245034

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