Acetic Acid → 2-Cyclopropylamino-4,5-difluorobenzoic acid

HRID 729387

Reaktionsgleichung

Reaktionsgleichung von HRID 729387
[F:1][C:2]1[CH:3]=[C:4]([NH2:12])[C:5](=[CH:9][C:10]=1[F:11])[C:6]([OH:8])=[O:7].C(O)(=O)C.C(O[C:20]1(O[Si](C)(C)C)[CH2:22][CH2:21]1)C.C([BH3-])#N.[Na+]>CO.C(OCC)(=O)C>[CH:20]1([NH:12][C:4]2[CH:3]=[C:2]([F:1])[C:10]([F:11])=[CH:9][C:5]=2[C:6]([OH:8])=[O:7])[CH2:22][CH2:21]1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 7359652-Amino-4,5-difluorobenzoic acidHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 149974732-Cyclopropylamino-4,5-difluorobenzoic acidAusbeute 94,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 4,5-difluoroanthranilic acid (1.13 g, 6.53 mmol) in anhydrous methanol (40 mL) is added molecular sieves (3 Å), acetic acid (3.70 mL, 65.3 mmol) and [(1-ethoxycyclopropyl)oxy]trimethylsilane (5.25 mL, 26.11 mmol). After 30 minutes, sodium cyanoborohydride (2.08 g, 32.64 mmol) is added, and the reaction mixture is heated to reflux. After 16 hours, the reaction is cooled to room temperature, filtered, washed with methanol, and the combined filtrate concentrated under vacuum to afford a viscous oil. The resulting oil is dissolved in ethyl acetate and washed with 1.0 M hydrochloric acid, water, and brine. The organic layer is dried over MgSO4, filtered, and the filtrate is concentrated under vacuum to afford as a beige solid (1.32 g). MS CI: m/z 212 (M+).

Aufarbeitung

  1. temperaturethe reaction mixture is heated to reflux
  2. waitAfter 16 hours
  3. filtrationfiltered
  4. washwashed with methanol
  5. concentrationthe combined filtrate concentrated under vacuum
  6. customto afford a viscous oil
  7. washwashed with 1.0 M hydrochloric acid, water, and brine
  8. dry with materialThe organic layer is dried over MgSO4
  9. filtrationfiltered
  10. concentrationthe filtrate is concentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-683fbc7e9aab429c86e45384ee7f4e3a
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582627B2

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