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

Potassium Carbonate → 1-(2-Tert-butoxy-2-oxoethyl)-4-(2-fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid

HRID 917724
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 917724
[C:1]([O:5][C:6](=[O:29])[CH2:7][N:8]1[C:13](=[O:14])[CH:12]=[C:11]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([I:22])=[CH:18][C:17]=2[F:23])[C:10]([C:24]([O:26]CC)=[O:25])=[CH:9]1)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+]>CCO.Cl>[C:1]([O:5][C:6](=[O:29])[CH2:7][N:8]1[C:13](=[O:14])[CH:12]=[C:11]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([I:22])=[CH:18][C:17]=2[F:23])[C:10]([C:24]([OH:26])=[O:25])=[CH:9]1)([CH3:4])([CH3:2])[CH3:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 11430Potassium CarbonateHCID 23631094Ethyl 1-(2-tert-butoxy-2-oxoethyl)-4-(2-fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxylate

Produkt 1

HCID 589628521-(2-Tert-butoxy-2-oxoethyl)-4-(2-fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxylic acidAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittel
HCID 702
Ethanol
Lösungsmittel

Versuchsvorschrift

Ethyl 1-(2-tert-butoxy-2-oxoethyl)-4-(2-fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxylate (510 mg, 0.99 mmol) was suspended in EtOH (120 mL), to which was added 1 M K2CO3 (80 mL). This mixture was stirred at R.T. for 15 h., then diluted with 1 M HCl (100 mL) and the resulting precipitate extracted into EtOAc (3×100 mL). The combined EtOAc fractions were washed with water (3×100 mL), brine (100 mL) and dried (Na2SO4). The solvent was then removed under reduced pressure to afford a crude solid which was purified by column chromatography on silica gel (5% MeOH/CH2Cl2 as eluant) to give 1-(2-tert-butoxy-2-oxoethyl)-4-(2-fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid as a white solid (64%), used directly in the next step. 1H NMR [(CD3)2SO, 400 MHz] δ 11.03 (v br s, 1H), 8.33 (s, 1H), 7.71 (dd, J=10.2, 1.9 Hz, 1H), 7.55 (dd, J=8.4, 1.0 Hz, 1H), 7.29 (t, J=8.3 Hz, 1H), 5.49 (s, 1H), 4.55 (s, 2H), 1.39 (s, 9H). HRMS (EI+) calcd C18H18FIN2O5 (M+) 488.0245, found 488.0247.

Aufarbeitung

  1. extractionthe resulting precipitate extracted into EtOAc (3×100 mL)
  2. washThe combined EtOAc fractions were washed with water (3×100 mL), brine (100 mL)
  3. dry with materialdried (Na2SO4)
  4. customThe solvent was then removed under reduced pressure
  5. customto afford a crude solid which
  6. customwas purified by column chromatography on silica gel (5% MeOH/CH2Cl2 as eluant)

Quellen und Nachweise

ORD-Eintrag
ord-8068e37d26204ba481ebc5939a495a65
Quelldatensatz
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07273877B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion