Dibenzofuran → (S)-4-dibenzofuran-2-yl-4-oxo-2-(2,2,2-trifluoroacetylamino)-butyric acid

HRID 376403

Reaktionsgleichung

Reaktionsgleichung von HRID 376403
[Cl-].[Al+3].[Cl-].[Cl-].[F:5][C:6]([F:18])([F:17])[C:7]([NH:9][C@@H:10]1[C:15](=[O:16])[O:14][C:12](=[O:13])[CH2:11]1)=[O:8].[CH:19]1[C:27]2[C:26]3[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=3[O:24][C:23]=2[CH:22]=[CH:21][CH:20]=1>ClCCl>[CH:19]1[C:27]2[C:26]3[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=3[O:24][C:23]=2[CH:22]=[CH:21][C:20]=1[C:12](=[O:13])[CH2:11][C@H:10]([NH:9][C:7](=[O:8])[C:6]([F:5])([F:18])[F:17])[C:15]([OH:16])=[O:14]

Komponenten

5

Edukt 3

HCID 568DibenzofuranHCID 6451240Aluminum(III) ChlorideHCID 12197622(S)-(-)-2-(Trifluoroacetamido)succinic anhydride

Produkt 1

HCID 54131944(S)-4-dibenzofuran-2-yl-4-oxo-2-(2,2,2-trifluoroacetylamino)-butyric acidAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a dichloromethane (50 mL) suspension of aluminum chloride (3.19 g, 0.024 mol) at 0° C., under an inert nitrogen atmosphere was added via a solid addition funnel an intimate mixture of N-trifluoroacetyl-L-aspartic acid anhydride (3.01 g, 0.0142 mol) and dibenzofuran (2 g, 0.0119 mol). The resulting brick-red suspension was allowed to warm to room temperature over 12 hours. The reaction mixture was poured into ice water (250 mL), and the resulting colorless biphasic mixture was extracted with ethyl acetate (4×100 mL). The combined organic extracts were washed with water (2×100 mL), brine (2×100 mL) and dried over magnesium sulfate. The mixture was filtered, and the organic solution was concentrated by evaporation of the solvent in vacuo to yield a white solid. The solid was recrystallized from 10% ethyl acetate/hexane (v/v) to give (S)-4-dibenzofuran-2-yl-4-oxo-2-(2,2,2-trifluoroacetylamino)-butyric acid (2.16 g, 48%) as a while solid; mp 174-176° C.

Aufarbeitung

  1. additionunder an inert nitrogen atmosphere was added via a solid addition funnel
  2. extractionthe resulting colorless biphasic mixture was extracted with ethyl acetate (4×100 mL)
  3. washThe combined organic extracts were washed with water (2×100 mL), brine (2×100 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe mixture was filtered
  6. concentrationthe organic solution was concentrated by evaporation of the solvent in vacuo
  7. customto yield a white solid
  8. customThe solid was recrystallized from 10% ethyl acetate/hexane (v/v)

Quellen und Nachweise

ORD-Eintrag
ord-36d7ccd7f5ce4ca6b2b4f941420f8764
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06020366

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