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Phosgene → 4-(4-Acryloylamino-benzenesulfonyl)-piperazine-1-carboxylic acid 2-chloro-benzyl ester

HRID 1841924
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1841924
[C:1](Cl)(Cl)=[O:2].[Cl:5][C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1[CH2:8][OH:9].[N:14]1([S:20]([C:23]2[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:33])[CH:31]=[CH2:32])=[CH:25][CH:24]=2)(=[O:22])=[O:21])[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C(N(C(C)C)CC)(C)C>C1COCC1.CN(C=O)C>[Cl:5][C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1[CH2:8][O:9][C:1]([N:17]1[CH2:16][CH2:15][N:14]([S:20]([C:23]2[CH:24]=[CH:25][C:26]([NH:29][C:30](=[O:33])[CH:31]=[CH2:32])=[CH:27][CH:28]=2)(=[O:21])=[O:22])[CH2:19][CH2:18]1)=[O:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 6371PhosgeneHCID 288102-Chlorobenzyl alcoholHCID 81531DiisopropylethylamineHCID 56953730N-[4-(piperazine-1-sulfonyl)-phenyl]-acrylamide

Produkt 1

HCID 529396444-(4-Acryloylamino-benzenesulfonyl)-piperazine-1-carboxylic acid 2-chloro-benzyl esterAusbeute 12 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Phosgene (0.5 ml, 20% solution in toluene) was added in one portion to a stirred solution of 2-chlorobenzyl alcohol (0.1 g, 0.7 mmol) in THF (2 ml) and the resulting mixture was stirred at room temperature under a nitrogen atmosphere for 3 hours. After this time the reaction mixture was concentrated under vacuum and the resulting residue was diluted with DMF (2 ml) and added drop wise to a stirred solution of N-[4-(piperazine-1-sulfonyl)-phenyl]-acrylamide (0.16 g, 0.54 mmol) and diisopropylethylamine (0.19 ml, 1.1 mmol) in DMF (4 ml). The resulting mixture was stirred at room temperature under a nitrogen atmosphere for 18 hours. After this time the reaction mixture was concentrated under vacuum and the residue was purified by Prep HPLC to give the title compound (0.029 g, 12% yield) as a white powder.

Aufarbeitung

  1. concentrationAfter this time the reaction mixture was concentrated under vacuum
  2. additionthe resulting residue was diluted with DMF (2 ml)
  3. stirringThe resulting mixture was stirred at room temperature under a nitrogen atmosphere for 18 hours
  4. concentrationAfter this time the reaction mixture was concentrated under vacuum
  5. customthe residue was purified by Prep HPLC

Quellen und Nachweise

ORD-Eintrag
ord-852b23af1f314c938a12cbf4ce4c30bc
Quelldatensatz
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08946197B2

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