Hydrochloric Acid → 5-Cyclohexyl-6-(2,2,2-trifluoroethoxy)nicotinic acid

HRID 240698

Reaktionsgleichung

Reaktionsgleichung von HRID 240698
C[O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([O:17][CH2:18][C:19]([F:22])([F:21])[F:20])=[C:9]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:10]=1)=[O:4].C1COCC1.O.[OH-].[Li+].Cl>O>[CH:11]1([C:9]2[CH:10]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=[N:7][C:8]=2[O:17][CH2:18][C:19]([F:21])([F:22])[F:20])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 71294015Methyl 5-cyclohexyl-6-(2,2,2-trifluoroethoxy)nicotinate

Produkt 1

HCID 712939525-Cyclohexyl-6-(2,2,2-trifluoroethoxy)nicotinic acidAusbeute 101,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

5-Cyclohexyl-6-(2,2,2-trifluoroethoxy)-3-pyridinecarboxylic acid methyl ester (95 mg, 299 μmol) was combined with THF (4 mL) and water (2 mL) to give a light yellow solution. Lithium hydroxide hydrate (25.1 mg, 599 μmol) was added under argon. The reaction mixture stirred at ambient temperature overnight, subsequently poured into 6 mL 2 M HCl and extracted with isopropyl acetate (2×60 mL). The organic layers were combined, dried with Na2SO4 and concentrated in vacuo to give the title compound (92 mg, quant.) as white solid; MS (ESI) 302.0 (M−H)−.

Aufarbeitung

  1. customto give a light yellow solution
  2. extractionextracted with isopropyl acetate (2×60 mL)
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-27e70c946e0c47efb7b623a35ddf5f23
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08648099B2

Verknüpfte Notizen

Wird geladen…