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Ethyl Acetate → (R)-3-{4-[4-(3,5-dichloropyridin-2-yl)piperazine-1-carbonyl]-2-fluorophenyl}-4-methoxymethyloxazolidin-2-one

HRID 1804243
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1804243
[F:1][C:2]1[CH:7]=[C:6]([C:8]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[O:9])[CH:5]=[CH:4][C:3]=1[N:16]1[C@H:20]([CH2:21][O:22][CH3:23])[CH2:19][O:18][C:17]1=[O:24].Cl[C:26]1[C:31]([Cl:32])=[CH:30][C:29]([Cl:33])=[CH:28][N:27]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[Cl:32][C:31]1[C:26]([N:13]2[CH2:14][CH2:15][N:10]([C:8]([C:6]3[CH:5]=[CH:4][C:3]([N:16]4[C@H:20]([CH2:21][O:22][CH3:23])[CH2:19][O:18][C:17]4=[O:24])=[C:2]([F:1])[CH:7]=3)=[O:9])[CH2:11][CH2:12]2)=[N:27][CH:28]=[C:29]([Cl:33])[CH:30]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 276662,3,5-TrichloropyridineHCID 58484520(R)-3-[2-fluoro-4-(piperazine-1-carbonyl)phenyl]-4-methoxymethyloxazolidin-2-one

Produkt 1

HCID 67381023(R)-3-{4-[4-(3,5-dichloropyridin-2-yl)piperazine-1-carbonyl]-2-fluorophenyl}-4-methoxymethyloxazolidin-2-oneAusbeute 48,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

(R)-3-[2-fluoro-4-(piperazine-1-carbonyl)phenyl]-4-methoxymethyloxazolidin-2-one (343 mg) described in Preparation Example 94 was dissolve in N,N-dimethylformamide (2 mL), 2,3,5-trichloropyridine (275 mg) and potassium carbonate (562 mg) were added and the mixture was stirred at 100° C. To the reaction mixture was added ethyl acetate under ice-cooling and insoluble materials were filtered off. Water was added to the filtrate and the mixture was extracted with ethyl acetate. The organic layer was washed twice with saturated brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography (chloroform:methanol) to give the title compound (240 mg).

Aufarbeitung

  1. temperaturecooling
  2. filtrationinsoluble materials were filtered off
  3. additionWater was added to the filtrate
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed twice with saturated brine
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by column chromatography (chloroform:methanol)

Quellen und Nachweise

ORD-Eintrag
ord-d0ef9fe2334f420e8ca0f70bd1621424
Quelldatensatz
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08354401B2

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