Methanol → 4-Aminothiazole-5-carboxylic acid ethyl ester

HRID 1161547Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1161547
CO.C1COCC1.[CH2:8]([O:10][C:11]([C:13]1[S:17][C:16](S(C)(=O)=O)=[N:15][C:14]=1[NH2:22])=[O:12])[CH3:9].[BH4-].[Na+]>O.C(OCC)(=O)C>[CH2:8]([O:10][C:11]([C:13]1[S:17][CH:16]=[N:15][C:14]=1[NH2:22])=[O:12])[CH3:9]

Komponenten

7

Edukt 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 59516885Ethyl 4-amino-2-(methylsulfonyl)-5-thiazolecarboxylate

Produkt 1

HCID 190176714-Aminothiazole-5-carboxylic acid ethyl esterAusbeute 81,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To 1 liter of a methanol:THF=1:1 mixed solvent solution containing 34.5 g of 4-amino-2-methanesulfonylthiazole-5-carboxylic acid ethyl ester, 10.4 g of sodium borohydride was added in small portions over a period of 20 minutes at room temperature. The reaction mixture was stirred at room temperature for 2 hours, and then was poured into 8 liters of ethyl acetate and 4 liters of water. The organic layer was washed with 3 liters of water and 3 liters of saturated brine, and the aqueous layer was extracted with ethyl acetate again. The organic layers were combined and dried over anhydrous magnesium sulfate. The desiccating agent was removed by filtration, and the filtrate was concentrated under reduced pressure to give the title compound (19.3 g) as a light yellow solid.

Aufarbeitung

  1. additionwas added in small portions over a period of 20 minutes at room temperature
  2. washThe organic layer was washed with 3 liters of water and 3 liters of saturated brine
  3. extractionthe aqueous layer was extracted with ethyl acetate again
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe desiccating agent was removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ec707d28489c47b1bccd6cd1b7585fc6
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07816522B2

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