Hydrochloric Acid → 2-(2,3,4-Trifluoroanilino)propionic acid

HRID 8454

Reaktionsgleichung

Reaktionsgleichung von HRID 8454
CC(C)([O-])C.[K+].[F:7][C:8]1[C:20]([F:21])=[C:19]([F:22])[CH:18]=[CH:17][C:9]=1[NH:10][C@H:11]([CH3:16])[C:12]([O:14]C)=[O:13].[OH-].[Na+].Cl>CC(N(C)C)=O>[F:7][C:8]1[C:20]([F:21])=[C:19]([F:22])[CH:18]=[CH:17][C:9]=1[NH:10][CH:11]([CH3:16])[C:12]([OH:14])=[O:13]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10149157Methyl (2R)-2-(2,3,4-trifluoroanilino)propionateHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 220158662-(2,3,4-Trifluoroanilino)propionic acidAusbeute 98,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel2×

Versuchsvorschrift

Potassium tertiary-butoxide (123.4 mg) was suspended in DMAc (2 ml). Under ice-cooling, a solution of methyl (2R)-2-(2,3,4-trifluoroanilino)propionate (223 mg, 91% ee) in DMAc (2 ml) was added thereto. The liquid reaction mixture was stirred at the same temperature for 1 hour. Then an aqueous solution of sodium hydroxide (3 mol/l; 2 ml) was added and the mixture was stirred for 1 hour. The liquid reaction mixture was adjusted to pH 2 with an aqueous solution of hydrochloric acid (3 mol/l) and then extracted with IPE. The organic layer was dried over anhydrous magnesium sulfate and evaporated. The crude product thus obtained was recrystallized from a solvent mixture of methylene chloride with normal hexane to thereby give the title compound (206 mg) as colorless crystals. The optical purity of this product was 0% ee. Various spectral data of this product was identical with those obtained in Example 23.

Aufarbeitung

  1. temperatureUnder ice-cooling
  2. customThe liquid reaction mixture
  3. stirringthe mixture was stirred for 1 hour
  4. customThe liquid reaction mixture
  5. extractionextracted with IPE
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customevaporated
  8. customThe crude product thus obtained
  9. customwas recrystallized from a solvent mixture of methylene chloride with normal hexane

Quellen und Nachweise

ORD-Eintrag
ord-61b34c6c1be54403acdd2d511f0f11ed
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087778B2

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