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

Oxalyl chloride → HCID 53935279, Verbindung

HRID 2268596
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2268596
C(Cl)(=O)C(Cl)=O.[C:7]([O:11][C:12]([N:14]([C:28]1[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=1)[CH2:15][CH2:16][O:17][C:18]1[CH:19]=[C:20]([CH:24]=[C:25]([Cl:27])[CH:26]=1)[C:21](O)=[O:22])=[O:13])([CH3:10])([CH3:9])[CH3:8].[C:34]1([NH:40][CH2:41][CH2:42][S:43]([F:46])(=[O:45])=[O:44])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.CCN(C(C)C)C(C)C>ClCCl.CN(C=O)C.CN(C1C=CN=CC=1)C>[C:7]([O:11][C:12](=[O:13])[N:14]([CH2:15][CH2:16][O:17][C:18]1[CH:19]=[C:20]([C:21](=[O:22])[N:40]([CH2:41][CH2:42][S:43]([F:46])(=[O:45])=[O:44])[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:24]=[C:25]([Cl:27])[CH:26]=1)[C:28]1[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=1)([CH3:9])([CH3:8])[CH3:10]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 125534362-Anilinoethane-1-sulfonyl fluorideHCID 18348849Benzoic acid,3-chloro-5-[2-[[(1,1-dimethylethoxy)carbonyl]-4-pyridinylamino]ethoxy]-

Produkt 1

HCID 53935279HCID 53935279, VerbindungAusbeute 54,7 %

Reagenzien, Katalysatoren, Lösungsmittel

3
HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

2M Oxalyl chloride solution in dichloromethane (0.9 ml) and DMF (0.025 ml) were added to a suspension of 3-[2-(tert-butoxycarbonyl-pyridin-4-yl-amino)-ethoxy]-5-chloro-benzoic acid (0.610 g) in anhydrous dichloromethane (50 ml). The reaction was stirred at room temperature for 1 h then 2-phenylamino-ethanesulfonyl fluoride(0.257 g), DMAP (0.018 g) and DIPEA (0.261 ml) were added. The reaction mixture was stirred at room temperature for 20 h and partitioned between ethyl acetate and 1M aqueous hydrochloric acid. The aqueous layer was removed and the organic phase washed with saturated aqueous sodium bicarbonate, water and dried with brine and over sodium sulphate and concentrated under reduced pressure. The residue was purified by flash column chromatography, eluting with using ethyl acetate:petroleum ether (3:1 v/v) to give the title compound as a white foam (0.40 g).

Aufarbeitung

  1. stirringThe reaction mixture was stirred at room temperature for 20 h
  2. custompartitioned between ethyl acetate and 1M aqueous hydrochloric acid
  3. customThe aqueous layer was removed
  4. washthe organic phase washed with saturated aqueous sodium bicarbonate, water
  5. dry with materialdried with brine and over sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography
  8. washeluting with using ethyl acetate:petroleum ether (3:1 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-4fc8f36d09a449e7b16f24282b5d1540
Quelldatensatz
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06326386B1

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion