2-Mercapto-2-methylpropanoic acid → 2-{[2-(3,5-Difluorophenyl)-2-oxoethyl]thio}-2-methylpropanoic acid

HRID 1866608

Reaktionsgleichung

Reaktionsgleichung von HRID 1866608
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([F:12])[CH:11]=1)[C:5](=[O:8])[CH2:6]Br.C(=O)(O)[O-].[Na+].[SH:18][C:19]([CH3:24])([CH3:23])[C:20]([OH:22])=[O:21]>C1COCC1.O.C(OCC)C.Cl>[F:1][C:2]1[CH:3]=[C:4]([C:5](=[O:8])[CH2:6][S:18][C:19]([CH3:24])([CH3:23])[C:20]([OH:22])=[O:21])[CH:9]=[C:10]([F:12])[CH:11]=1

Komponenten

8

Edukt 3

HCID 784212-Mercapto-2-methylpropanoic acidHCID 516892Sodium BicarbonateHCID 27783312-Bromo-1-(3,5-difluorophenyl)ethanone

Produkt 1

HCID 669733052-{[2-(3,5-Difluorophenyl)-2-oxoethyl]thio}-2-methylpropanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 313Hydrochloric AcidLösungsmittelHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 3,5-difluorophenacyl bromide (845 mg, 3.60 mmol) in THF (12 mL) and water (12 mL) was added sodium bicarbonate (317 mg, 3.78 mmol) and 2-mercaptoisobutyric acid (432 mg, 3.60 mmol). The reaction mixture was allowed to stir at ambient temperature for 1.0 h under a stream of nitrogen. The reaction mixture was diluted with diethyl ether (50 mL) and 1 M HCl (15 mL). The organic layer was then washed with 20 mL saturated brine. The organics were then dried over sodium sulfate, filtered and concentrated in vacuo to give the title compound, which was used without further purification. MS: m/z=229 (M−CO2H).

Aufarbeitung

  1. washThe organic layer was then washed with 20 mL saturated brine
  2. dry with materialThe organics were then dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-49e89eca02ac408497475da47ed5bce4
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07629338B2

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