Lithium Hydroxide → [4-Difluoromethoxy-2-ethyl-8-fluoro-3-(4-pyrazol-1-yl-benzyl)quinolin-5-yloxy]acetic acid

HRID 1922065Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1922065
C[O:2][C:3](=[O:35])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]2[C:7]=1[C:8]([O:31][CH:32]([F:34])[F:33])=[C:9]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]3[CH:30]=[CH:29][CH:28]=[N:27]3)=[CH:22][CH:21]=1)[C:10]([CH2:17][CH3:18])=[N:11]2.[OH-].[Li+]>O1CCCC1>[F:34][CH:32]([F:33])[O:31][C:8]1[C:7]2[C:12](=[C:13]([F:16])[CH:14]=[CH:15][C:6]=2[O:5][CH2:4][C:3]([OH:35])=[O:2])[N:11]=[C:10]([CH2:17][CH3:18])[C:9]=1[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH:30]=[CH:29][CH:28]=[N:27]2)=[CH:22][CH:21]=1

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 67458307[4-Difluoromethoxy-2-ethyl-8-fluoro-3-(4-pyrazol-1-ylbenzyl)quinolin-5-yloxy]acetic acid methyl ester

Produkt 1

HCID 24995212[4-Difluoromethoxy-2-ethyl-8-fluoro-3-(4-pyrazol-1-yl-benzyl)quinolin-5-yloxy]acetic acidAusbeute 97,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of [4-difluoromethoxy-2-ethyl-8-fluoro-3-(4-pyrazol-1-ylbenzyl)quinolin-5-yloxy]acetic acid methyl ester (0.19 g) in tetrahydrofuran (5.0 mL) was treated with 1.0 M aqueous lithium hydroxide solution (0.78 mL), and the resulting solution was stirred at room temperature for 1 hour. The tetrahydrofuran was removed under reduced pressure and the residue acidified by the addition of 0.1 M aqueous hydrochloric acid. The mixture was extracted with ethyl acetate and the combined extracts were washed with saturated aqueous sodium chloride solution, and then dried over magnesium sulfate. The solvent was removed under reduced pressure to afford title compound (0.18 g).

Aufarbeitung

  1. customThe tetrahydrofuran was removed under reduced pressure
  2. additionthe residue acidified by the addition of 0.1 M aqueous hydrochloric acid
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe combined extracts were washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-35e50a6babaa4b19b325fc303af5b49e
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173812B2

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