Hydrochloric Acid → 6-[3-(4-Fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-nicotinic acid

HRID 1514679Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1514679
C[O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)=[N:14][O:15][C:16]=2[CH2:17][OH:18])=[N:6][CH:5]=1.[OH-].[Li+].Cl.C(OCC)(=O)C>C1COCC1.CO.O>[F:25][C:22]1[CH:23]=[CH:24][C:19]([C:13]2[C:12]([CH2:11][O:10][C:7]3[CH:8]=[CH:9][C:4]([C:3]([OH:26])=[O:2])=[CH:5][N:6]=3)=[C:16]([CH2:17][OH:18])[O:15][N:14]=2)=[CH:20][CH:21]=1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 667181316-[3-(4-Fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester

Produkt 1

HCID 667181506-[3-(4-Fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-nicotinic acidAusbeute 104,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To 6-[3-(4-fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester (1.00 g, 2.79 mmol) in THF (6.25 mL), methanol (1.75 mL) and water (6.25 mL) was added lithium hydroxide (136 mg, 5.58 mmol). The reaction mixture was stirred overnight at room temperature. Addition of aqueous hydrochloride solution (1 N, 100 mL) and extraction with ethyl acetate yielded the title compound (1.00 g, 100%) as a white solid. MS: m/e=345.2 [M+H]+.

Quellen und Nachweise

ORD-Eintrag
ord-194a23ea318b479299c1c5d8a8358b6e
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222246B2

Notizen zur Reaktion

Wird geladen…