Lithium Hydroxide → 3-[4-(azetidin-1-ylcarbonyl)-2-fluorophenoxy]-5-[(1S)-2-hydroxy-1-methylethoxy]benzoic acid

HRID 20504Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 20504
[N:1]1([C:5]([C:7]2[CH:28]=[CH:27][C:10]([O:11][C:12]3[CH:13]=[C:14]([CH:19]=[C:20]([O:22][C@@H:23]([CH3:26])[CH2:24][OH:25])[CH:21]=3)[C:15]([O:17]C)=[O:16])=[C:9]([F:29])[CH:8]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1.[OH-].[Li+]>C1COCC1.O>[N:1]1([C:5]([C:7]2[CH:28]=[CH:27][C:10]([O:11][C:12]3[CH:13]=[C:14]([CH:19]=[C:20]([O:22][C@@H:23]([CH3:26])[CH2:24][OH:25])[CH:21]=3)[C:15]([OH:17])=[O:16])=[C:9]([F:29])[CH:8]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 59346922Methyl 3-[4-(azetidin-1-ylcarbonyl)-2-fluorophenoxy]-5-[(1S)-2-hydroxy-1-methylethoxy]benzoate

Produkt 1

HCID 593468833-[4-(azetidin-1-ylcarbonyl)-2-fluorophenoxy]-5-[(1S)-2-hydroxy-1-methylethoxy]benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Methyl 3-[4-(azetidin-1-ylcarbonyl)-2-fluorophenoxy]-5-[(1S)-2-hydroxy-1-methylethoxy]benzoate (100 mg, 0.25 mmol) was dissolved in THF (2.0 mL and water (0.2 mL) and solid lithium hydroxide (21 mg, 0.5 mmol) added. The resultant mixture was stirred at ambient temperature for 16 hours. Water (10 mL) was added and the mixture partially reduced in vacuo and then extracted with ethyl acetate. The aqueous liquors were acidified with 1M hydrochloric acid and re-extracted with ethyl acetate (2×10 mL). The extracts were combined, washed with brine, dried (MgSO4), filtered, and evaporated in vacuo to give the crude product which was used without further purification (70 mg).

Aufarbeitung

  1. additionadded
  2. extractionextracted with ethyl acetate
  3. extractionre-extracted with ethyl acetate (2×10 mL)
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1ecbd50443124bb3bd783689e52ee0b1
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745475B2

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