Citric Acid → HCID 66939284, Verbindung

HRID 1257412Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1257412
[H-].[Na+].[NH:3]1[CH:7]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:5]=[N:4]1.Cl[CH2:14][C:15]1[N:16]=[C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[C:21]=2[F:30])[O:18][CH:19]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O.C(OCC)(=O)C>[F:30][C:21]1[C:22]([C:26]([F:29])([F:27])[F:28])=[CH:23][CH:24]=[CH:25][C:20]=1[C:17]1[O:18][CH:19]=[C:15]([CH2:14][N:3]2[CH:7]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:5]=[N:4]2)[N:16]=1

Komponenten

7

Edukt 4

HCID 311Citric AcidHCID 24758Sodium hydrideHCID 142179ethyl 1H-pyrazole-4-carboxylateHCID 66939077HCID 66939077, Verbindung

Produkt 1

HCID 66939284HCID 66939284, VerbindungAusbeute 76,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a suspension of sodium hydride (60% in mineral oil, 0.08 g) in N,N-dimethylformamide (2 ml) was added ethyl 1H-pyrazole-4-carboxylate (0.21 g). After stirring at room temperature for 30 min, the compound (0.42 g) obtained in Example 105a was added to the reaction mixture. After stirring at room temperature for 2 hr, 10% aqueous citric acid solution and ethyl acetate were added to the reaction mixture. The ethyl acetate layer was separated, washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate) to give the title compound (0.44 g) as colorless crystals.

Aufarbeitung

  1. stirringAfter stirring at room temperature for 2 hr
  2. customThe ethyl acetate layer was separated
  3. washwashed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-3624be0252f54fda92bdafc92c3a5965
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461348B2

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