Hydrochloric Acid → 5-[3-(4-Chloro-phenyl)-isoxazol-4-ylmethoxy]-pyrazine-2-carboxylic acid

HRID 600498Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 600498
C[O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([O:11][CH2:12][C:13]2[C:14]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)=[N:15][O:16][CH:17]=2)=[CH:7][N:6]=1)=[O:4].O.[OH-].[Li+].Cl>C1COCC1.O.CO>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([C:14]2[C:13]([CH2:12][O:11][C:8]3[N:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[N:6][CH:7]=3)=[CH:17][O:16][N:15]=2)=[CH:19][CH:20]=1

Komponenten

7

Edukt 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 671578395-[3-(4-Chloro-phenyl)-isoxazol-4-ylmethoxy]-pyrazine-2-carboxylic acid methyl ester

Produkt 1

HCID 684440725-[3-(4-Chloro-phenyl)-isoxazol-4-ylmethoxy]-pyrazine-2-carboxylic acidAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 5-[3-(4-chloro-phenyl)-isoxazol-4-ylmethoxy]-pyrazine-2-carboxylic acid methyl ester (1.0 g, 2.89 mmol) in THF (6.3 mL), water (6.3 mL) and methanol (1.75 mL) was added lithium hydroxide monohydrate (141.4 mg, 5.78 mmol) and the resulting mixture stirred at room temperature for 2 h and then acidified with HCl (4 N) and extracted with ethyl acetate. The combined organic layers were then washed with water and brine, dried over sodium sulfate and evaporated to afford the title product (360 mg, 38%) which was obtained as white solid. MS: m/e=330.0 [M−H]−.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were then washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-7dcac29b8493406e938023b0c114286c
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902201B2

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