Water → 2-(4-Amino-3-fluorophenyl)-6,8-difluoro-5-(4-methyl-3-pentenylamino)-4H-1-benzopyran-4-one

HRID 1736215Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1736215
C(OC([N:8]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[O:19][C:20]3[C:28]([F:29])=[CH:27][C:26]([F:30])=[C:25]([NH:31][CH2:32][CH2:33][CH:34]=[C:35]([CH3:37])[CH3:36])[C:21]=3[C:22](=[O:24])[CH:23]=2)=[CH:14][C:13]=1[F:38])COC)=O)(C)(C)C.S(=O)(=O)(O)O.O>C(O)C>[NH2:8][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[O:19][C:20]3[C:28]([F:29])=[CH:27][C:26]([F:30])=[C:25]([NH:31][CH2:32][CH2:33][CH:34]=[C:35]([CH3:36])[CH3:37])[C:21]=3[C:22](=[O:24])[CH:23]=2)=[CH:14][C:13]=1[F:38]

Komponenten

5

Edukt 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 194348222-[4-[N-(tert-butoxycarbonyl)-N-methoxymethylamino]-3-fluorophenyl]-6,8-difluoro-5-(4-methyl-3-pentenylamino)-4H-1-benzopyran-4-one

Produkt 1

HCID 194349092-(4-Amino-3-fluorophenyl)-6,8-difluoro-5-(4-methyl-3-pentenylamino)-4H-1-benzopyran-4-oneAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

1.03 g (1.94 mmol) of the above 2-[4-[N-(tert-butoxycarbonyl)-N-methoxymethylamino]-3-fluorophenyl]-6,8-difluoro-5-(4-methyl-3-pentenylamino)-4H-1-benzopyran-4-one was dissolved in 80 mL of ethanol, 20 mL of 50% sulfuric acid was added and the mixture was stirred at room temperature for 18 hours. Water was added to the reaction solution and the mixture was extracted twice with ethyl acetate. The organic layer was washed once with an aqueous saturated solution of sodium bicarbonate, once with water and once with an aqueous saturated solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:2-2:1) to give 520 mg of Compound 137 (yield: 69%).

Aufarbeitung

  1. extractionthe mixture was extracted twice with ethyl acetate
  2. washThe organic layer was washed once with an aqueous saturated solution of sodium bicarbonate, once with water and once with an aqueous saturated solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:2-2:1)

Quellen und Nachweise

ORD-Eintrag
ord-64dbb16da52541278155aaf404452d68
Quelldatensatz
uspto-grants-1996_07
Patentnummer
US05539112

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