Lithium hydroxide, monohydrate → 3-fluoro-4-(3-[(1S)-2-hydroxy-1-methylethoxy]-5-{[(1-methyl-1H-pyrazol-3-yl)amino]carbonyl}phenoxy)benzoic acid

HRID 20570Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 20570
[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[O:13][C:14]1[CH:19]=[C:18]([C:20]([NH:22][C:23]2[CH:27]=[CH:26][N:25]([CH3:28])[N:24]=2)=[O:21])[CH:17]=[C:16]([O:29][C@@H:30]([CH3:33])[CH2:31][OH:32])[CH:15]=1)[C:5]([O:7]CC)=[O:6].O.[OH-].[Li+]>C1COCC1.O>[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[O:13][C:14]1[CH:19]=[C:18]([C:20]([NH:22][C:23]2[CH:27]=[CH:26][N:25]([CH3:28])[N:24]=2)=[O:21])[CH:17]=[C:16]([O:29][C@@H:30]([CH3:33])[CH2:31][OH:32])[CH:15]=1)[C:5]([OH:7])=[O:6]

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 59346875ethyl 3-fluoro-4-(3-[(1S)-2-hydroxy-1-methylethoxy]-5-{[(1-methyl-1H-pyrazol-3-yl)amino]carbonyl}phenoxy)benzoate

Produkt 1

HCID 593469353-fluoro-4-(3-[(1S)-2-hydroxy-1-methylethoxy]-5-{[(1-methyl-1H-pyrazol-3-yl)amino]carbonyl}phenoxy)benzoic acidAusbeute 95,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of ethyl 3-fluoro-4-(3-[(1S)-2-hydroxy-1-methylethoxy]-5-{[(1-methyl-1H-pyrazol-3-yl)amino]carbonyl}phenoxy)benzoate (1.8 g, 3.94 mmol) in THF (60 mL) was added to a solution of lithium hydroxide monohydrate (0.83 g, 19.7 mmol) in water (30 mL). The mixture was stirred at RT for 72 hours and the THF removed in vacuo. The aqueous layer was extracted into ethyl acetate (100 mL) to remove any impurities, then acidified with 1M hydrochloric acid and extracted into ethyl acetate (2×100 mL). The combined extracts were dried (MgSO4) and the solvent removed in vacuo to give the desired compound (1.62 g).

Aufarbeitung

  1. customthe THF removed in vacuo
  2. extractionThe aqueous layer was extracted into ethyl acetate (100 mL)
  3. customto remove any impurities
  4. extractionextracted into ethyl acetate (2×100 mL)
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-41a5948e1e0b4d4c9514b05e524fd593
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745475B2

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