StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

1,2-Dichloroethane → 4-[4-(1-Oxo-but-2-ynylamino)-benzenesulfonyl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 1841918
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1841918
[C:1]([OH:6])(=O)[C:2]#[C:3][CH3:4].N1C=CC=CC=1.[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][N:23]([S:26]([C:29]2[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][CH:30]=2)(=[O:28])=[O:27])[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].C(Cl)CCl>C1COCC1.CC(N(C)C)=O.C(OCC)(=O)C>[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][N:23]([S:26]([C:29]2[CH:30]=[CH:31][C:32]([NH:35][C:1](=[O:6])[C:2]#[C:3][CH3:4])=[CH:33][CH:34]=2)(=[O:28])=[O:27])[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:14])[CH3:15]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 111,2-DichloroethaneHCID 1049PyridineHCID 685352-Butynoic acidHCID 10617209tert-Butyl 4-(4-aminophenylsulfonyl)piperazine-1-carboxylate

Produkt 1

HCID 569547204-[4-(1-Oxo-but-2-ynylamino)-benzenesulfonyl]-piperazine-1-carboxylic acid tert-butyl esterAusbeute 20,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 69293768tetrahydrofuran N,N-dimethylacetamideLösungsmittel

Versuchsvorschrift

But-2-ynoic acid (0.19 g, 2.36 mmol) followed by pyridine (0.6 ml), were added sequentially portion wise to a stirred solution of 4-(4-amino-benzenesulfonyl)-piperazine-1-carboxylic acid tert-butyl ester (0.2 g, 0.59 mmol) in THF/DMA (3:2, 5 ml) at room temperature. To this mixture was added EDC (0.6 g, 3.1 mmol) in one portion and the mixture was stirred at room temperature under a nitrogen atmosphere for 1 hour. After this time the mixture was diluted with ethyl acetate (50 ml) and washed with water (100 ml), saturated NaHCO3 (100 ml) and HCl (100 ml, 2M). The organic layer was separated, dried (MgSO4), filtered and concentrated under vacuum and the resulting residue was purified by flash column chromatography (elution, 20% ethyl acetate, 80% DCM) to give the title compound (0.05 g, 19% yield) as a white solid. Tr=4.12 min, m/z (ES+) (M+Na)+ 430.

Aufarbeitung

  1. washwashed with water (100 ml), saturated NaHCO3 (100 ml) and HCl (100 ml, 2M)
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customthe resulting residue was purified by flash column chromatography (elution, 20% ethyl acetate, 80% DCM)

Quellen und Nachweise

ORD-Eintrag
ord-c8e797c64b3f47c9883cc0d88d728f0a
Quelldatensatz
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08946197B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion