Potassium Carbonate → HCID 69061077, Verbindung

HRID 490141Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 490141
S(Cl)(Cl)=O.[CH3:5][O:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][C:8]=1[C:15]1(O)[C:23]2[C:18](=[CH:19][C:20]([O:26][CH3:27])=[C:21]([O:24][CH3:25])[CH:22]=2)[NH:17][C:16]1=[O:28].[F:30][C@H:31]1[CH2:35][NH:34][C@H:33]([C:36]([N:38]([CH3:40])[CH3:39])=[O:37])[CH2:32]1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.C(N(CC)CC)C.C(Cl)(Cl)Cl.N1C=CC=CC=1>[CH3:5][O:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][C:8]=1[C:15]1([N:34]2[CH2:35][C@H:31]([F:30])[CH2:32][C@H:33]2[C:36]([N:38]([CH3:40])[CH3:39])=[O:37])[C:23]2[C:18](=[CH:19][C:20]([O:26][CH3:27])=[C:21]([O:24][CH3:25])[CH:22]=2)[NH:17][C:16]1=[O:28]

Komponenten

9

Edukt 4

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 231206493-(2,4-dimethoxyphenyl)-3-hydroxy-5,6-dimethoxy-1,3-dihydro-2H-indol-2-oneHCID 57673967HCID 57673967, Verbindung

Produkt 1

HCID 69061077HCID 69061077, VerbindungAusbeute 70,5 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 1049PyridineLösungsmittelHCID 6212ChloroformLösungsmittel2×HCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

362 mL of thionyl chloride was added at −78° C. and under a nitrogen gas flow to a 14 mL chloroform solution of 700 mg of the compound obtained in step 9-1 and 240 mg of pyridine, and the reaction mixture was stirred for 30 minutes at the same temperature. After this, a 5 mL chloroform solution of 485 mg of the compound obtained in step 9-2 and 2.05 g of triethylamine was added over a period of 2 minutes, after which the temperature was raised to room temperature and the reaction mixture was stirred for 15 hours at that temperature. 50 mL of ethyl acetate and 30 mL of a 5% potassium carbonate aqueous solution were added to the reaction solution, and the reaction mixture was stirred for 5 minutes. After liquid separation, the aqueous layer was extracted with ethyl acetate (30 mL×2), the combined organic layer was washed with saturated brine and dried with magnesium sulfate, the drying agent was filtered off, and the reaction mixture was concentrated under reduced pressure. The residue thus obtained was purified by column chromatography (silica gel 60N, mobile phase: ethyl acetate/acetone=1/1; v/v) to obtain 697 mg of mixture of diastereoisomers of the titled compound (reddish-brown, amorphous).

Aufarbeitung

  1. stirringthe reaction mixture was stirred for 15 hours at that temperature
  2. stirringthe reaction mixture was stirred for 5 minutes
  3. customAfter liquid separation
  4. extractionthe aqueous layer was extracted with ethyl acetate (30 mL×2)
  5. washthe combined organic layer was washed with saturated brine
  6. dry with materialdried with magnesium sulfate
  7. filtrationthe drying agent was filtered off
  8. concentrationthe reaction mixture was concentrated under reduced pressure
  9. customThe residue thus obtained
  10. customwas purified by column chromatography (silica gel 60N, mobile phase: ethyl acetate/acetone=1/1; v/v)

Quellen und Nachweise

ORD-Eintrag
ord-10e2ddc4ba214c43bb6bdce3a2c9401f
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07528124B2

Notizen zur Reaktion

Wird geladen…