Tetrahydrofuran → 2-(benzyloxy)-N-(5-cyano-2-fluoro-3-hydroxy-6-methylbiphenyl-4-yl)acetamide

HRID 17346Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 17346
[CH2:1]([O:8][CH2:9][C:10](Cl)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1.[NH2:18][C:19]1[C:26]([OH:27])=[C:25]([F:28])[C:24]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:23]([CH3:35])[C:20]=1[C:21]#[N:22].C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[CH2:1]([O:8][CH2:9][C:10]([NH:18][C:19]1[C:26]([OH:27])=[C:25]([F:28])[C:24]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:23]([CH3:35])[C:20]=1[C:21]#[N:22])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 177085Benzyloxyacetyl chlorideHCID 516892Sodium BicarbonateHCID 860974464-Amino-3-cyano-6-fluoro-5-hydroxy-2-methylbiphenyl

Produkt 1

HCID 866308382-(benzyloxy)-N-(5-cyano-2-fluoro-3-hydroxy-6-methylbiphenyl-4-yl)acetamideAusbeute 77,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Under nitrogen atmosphere, benzyloxyacetyl chloride (489 μl, 3.10 mmol) was dropwise added to a tetrahydrofuran solution (10 ml) of 2-amino-5-phenyl-4-fluoro-3-hydroxy-6-methylbenzonitrile (I-41) (500 mg, 2.06 mmol) and sodium hydrogencarbonate (520 mg, 6.19 mmol) cooled with ice, followed by stirring at room temperature for 18 hours. Ethyl acetate was added to the reaction liquid, followed by washing with water and saturated brine. The obtained organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated away under reduced pressure. The resulting residue was recrystallized and purified with n-hexane/ethyl acetate to obtain the entitled compound (621 mg, 1.59 mmol, 77%) as a white solid.

Aufarbeitung

  1. temperaturecooled with ice
  2. washby washing with water and saturated brine
  3. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated away under reduced pressure
  5. customThe resulting residue was recrystallized
  6. custompurified with n-hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-f3c7c2d7056b4b81b49efd7fc92c0797
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737166B2

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