1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Di-tert-butyl 4-(3-((6-chloro-2-naphthyl)sulfonyl)propanoyl)piperazine-1,3-dicarboxylate

HRID 493713Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 493713
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([CH2:15][CH2:16][C:17]([OH:19])=O)(=[O:14])=[O:13])[CH:6]=[CH:5]2.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[N:41]1([C:54]([O:56][C:57]([CH3:60])([CH3:59])[CH3:58])=[O:55])[CH2:46][CH2:45][NH:44][CH:43]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[CH2:42]1>C(N(CC)CC)C.C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([CH2:15][CH2:16][C:17]([N:44]1[CH2:45][CH2:46][N:41]([C:54]([O:56][C:57]([CH3:58])([CH3:59])[CH3:60])=[O:55])[CH2:42][CH:43]1[C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])=[O:19])(=[O:13])=[O:14])[CH:6]=[CH:5]2

Komponenten

7

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 2756817n-4-Boc-2-piperazinecarboxylic acid tert-butyl esterHCID 111973043-(6-Chloro-2-naphthyl)sulfonylpropionic acid

Produkt 1

HCID 23130894Di-tert-butyl 4-(3-((6-chloro-2-naphthyl)sulfonyl)propanoyl)piperazine-1,3-dicarboxylateAusbeute 383,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

3-((6-Chloro-2-naphthyl)sulfonyl)propanoic acid (0.33 g), HOBt (2.30 g) and WSC (2.88 g) were added to acetonitrile (50 mL) and mixed for 15 minutes. Then, di-tert-butyl piperazine-1,3-dicarboxylate (2.99 g) and triethylamine (3.03 g) were added thereto, and the mixture was mixed at room temperature for 15 hours. The reaction solution was concentrated under reduced pressure, and the residue was diluted with ethyl acetate and an aqueous potassium carbonate solution. The organic layer was collected by separation, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified with a silica gel column to give the title compound (2.40 g) as a colorless powder.

Aufarbeitung

  1. additionmixed for 15 minutes
  2. additionthe mixture was mixed at room temperature for 15 hours
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. additionthe residue was diluted with ethyl acetate
  5. customThe organic layer was collected by separation
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off
  8. customthe residue was purified with a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-896469730cd045fa8a5ab651660a0b28
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07534887B2

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