Water → 3-[[3,3-Difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-pyridine-4-carboxylic acid

HRID 925269

Reaktionsgleichung

C[O:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[S:11][CH2:12][CH2:13][C:14]([F:23])([F:22])[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)=[O:4].[OH-].[Na+].O>CCO>[F:23][C:14]([F:22])([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)[CH2:13][CH2:12][S:11][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][C:5]=1[C:3]([OH:4])=[O:2]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a solution of 3-[[3,3-difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-pyridine-4-carboxylic acid methyl ester (0.33 g, 0.96 mmol) in EtOH (10 ml) are added sodium hydroxide (0.15 g, 3.87 mmol) and water (10 ml). The reaction mixture is stirred at 80° C. for 1 h. After completion of the reaction, the solvent is evaporated and the residue is diluted with water (10 ml). The aqueous layer is acidified with 2M hydrochloric acid to pH 3 and extracted with EtOAc (3×20 ml). The combined organic layers are washed with water (20 ml), brine (20 ml), dried over anhydrous sodium sulfate and evaporated to get the crude 3-[[3,3-difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-pyridine-4-carboxylic acid (0.26 g, 0.8 mmol, 82%), which is used in the next step without further purification.

Aufarbeitung

customAfter completion of the reaction
customthe solvent is evaporated
additionthe residue is diluted with water (10 ml)
extractionextracted with EtOAc (3×20 ml)
washThe combined organic layers are washed with water (20 ml), brine (20 ml)
dry with materialdried over anhydrous sodium sulfate
customevaporated

Quellen und Nachweise

ORD-Eintrag: ord-d6a583cd36e34a19a84921fd10b457b6
Quelldatensatz: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09284286B2

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