Lithium hydroxide, monohydrate → 3-{[5-(azetidin-1-ylcarbonyl)-3-chloropyridin-2-yl]oxy}-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}benzoic acid

HRID 1175985Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1175985
O.[OH-].[Li+].[N:4]1([C:8]([C:10]2[CH:11]=[C:12]([Cl:32])[C:13]([O:16][C:17]3[CH:18]=[C:19]([CH:24]=[C:25]([O:27][C@@H:28]([CH3:31])[CH2:29][OH:30])[CH:26]=3)[C:20]([O:22]C)=[O:21])=[N:14][CH:15]=2)=[O:9])[CH2:7][CH2:6][CH2:5]1>O.C1COCC1>[N:4]1([C:8]([C:10]2[CH:11]=[C:12]([Cl:32])[C:13]([O:16][C:17]3[CH:18]=[C:19]([CH:24]=[C:25]([O:27][C@@H:28]([CH3:31])[CH2:29][OH:30])[CH:26]=3)[C:20]([OH:22])=[O:21])=[N:14][CH:15]=2)=[O:9])[CH2:7][CH2:6][CH2:5]1

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 53629688methyl 3-{[5-(azetidin-1-ylcarbonyl)-3-chloropyridin-2-yl]oxy}-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}benzoate

Produkt 1

HCID 591271743-{[5-(azetidin-1-ylcarbonyl)-3-chloropyridin-2-yl]oxy}-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}benzoic acidAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Lithium hydroxide monohydrate (529 mg, 12.59 mmol) in water (25 mL) was added to a solution of methyl 3-{[5-(azetidin-1-ylcarbonyl)-3-chloropyridin-2-yl]oxy}-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}benzoate (5.3 g, 12.6 mmol) in THF (50 mL) and stirred at RT for 3 hours. The THF was removed in vacuo and the aqueous layer was washed with ethyl acetate (50 mL) to remove any impurities. The aqueous layer was acidified and extracted into ethyl acetate (2×50 mL), and the organics washed with brine, dried (MgSO4), and concentrated in vacuo to give the desired compound as a white foam (3.74 g).

Aufarbeitung

  1. customThe THF was removed in vacuo
  2. washthe aqueous layer was washed with ethyl acetate (50 mL)
  3. customto remove any impurities
  4. extractionextracted into ethyl acetate (2×50 mL)
  5. washthe organics washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0dc6221eebe1458f8d088201638d72b7
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842694B2

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