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Carbon tetrabromide → HCID 68093205, Verbindung

HRID 1778412
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1778412
C(Br)(Br)(Br)Br.[C:6]([O:10][C:11]([N:13]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:14]1[C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18](O)[C:17]([C:25]2[C:29]([F:30])=[CH:28][O:27][C:26]=2[CH2:31][OH:32])=[CH:16][CH:15]=1)=[O:12])([CH3:9])([CH3:8])[CH3:7].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[C:6]([O:10][C:11]([N:13]([C:33]([O:35][C:36]([CH3:38])([CH3:37])[CH3:39])=[O:34])[C:14]1[C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18]2[C:17]([C:25]3[C:29]([F:30])=[CH:28][O:27][C:26]=3[CH2:31][O:32]2)=[CH:16][CH:15]=1)=[O:12])([CH3:8])([CH3:9])[CH3:7]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 68093039HCID 68093039, Verbindung2×

Produkt 1

HCID 68093205HCID 68093205, VerbindungAusbeute 63,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Carbon tetrabromide (2.74 g) was added to an ice-cooled solution of methyl 6-bis-(tert-butoxycarbonyl)amino-3-(4-fluoro-2-hydroxymethylfuran-3-yl)-2-hydroxybenzoate (Intermediate 99, 1.98 g) and triphenylphosphine (2.16 g) in DCM (70 mL). The mixture was stirred for 30 minutes and then concentrated in vacuo. The residue was dissolved in acetone (80 mL) and cesium carbonate (13.4 g) was added. The reaction mixture was heated at reflux for 30 minutes, cooled and then concentrated in vacuo. The residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate in cyclohexane, with a gradient of 0-30%. The resultant product was triturated with cyclohexane to give methyl 7-bis-(tert-butoxycarbonyl)amino-1-fluoro-4H-furo[2,3-c]chromene-6-carboxylate (1.21 g) as a white solid.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in acetone (80 mL)
  3. additioncesium carbonate (13.4 g) was added
  4. temperatureThe reaction mixture was heated
  5. temperatureat reflux for 30 minutes
  6. temperaturecooled
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography on silica
  9. washeluting with a mixture of ethyl acetate in cyclohexane, with a gradient of 0-30%
  10. customThe resultant product was triturated with cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-893f57477b2f4edba7854af89592eda1
Quelldatensatz
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09266896B2

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