Sodium Hydroxide → 5-((tert-Butoxycarbonyl)amino)-3-methylthiophene-2-carboxylic acid

HRID 446583Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 446583
[C:1]([O:5][C:6]([NH:8][C:9]1[S:13][C:12]([C:14]([O:16]C)=[O:15])=[C:11]([CH3:18])[CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C:6]([NH:8][C:9]1[S:13][C:12]([C:14]([OH:16])=[O:15])=[C:11]([CH3:18])[CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 14798Sodium Hydroxide2×HCID 58873954Methyl 5-[(tert-butoxycarbonyl)amino]-3-methylthiophene-2-carboxylate

Produkt 1

HCID 434168385-((tert-Butoxycarbonyl)amino)-3-methylthiophene-2-carboxylic acidAusbeute 71,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

The compound (1.81 g, 6.68 mmol) obtained in Example 30b was dissolved in methanol (27 mL), a 1 N aqueous sodium hydroxide solution (26.7 mL, 26.7 mmol) was added, and the mixture was stirred at 50° C. for 19.5 hours. A 1 N aqueous sodium hydroxide solution (26.7 mL, 26.7 mmol) was added to the reaction mixture, and the mixture was stirred at 50° C. for 24 hours. Methanol was evaporated under reduced pressure, water and ethyl acetate were added to the resulting residue, and the mixture was extracted with water (×2). The resulting aqueous layer was adjusted to pH 1 with 1 N hydrochloric acid, the mixture was extracted with ethyl acetate (×2), and then the organic layer was washed with saturated sodium chloride solution. The organic layer was dried with anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, and moisture was removed from the resulting residue azeotropically with toluene (×2) to give the title compound (1.23 g; yield, 62%) as a white solid.

Aufarbeitung

  1. stirringthe mixture was stirred at 50° C. for 24 hours
  2. customMethanol was evaporated under reduced pressure, water and ethyl acetate
  3. additionwere added to the resulting residue
  4. extractionthe mixture was extracted with water (×2)
  5. extractionthe mixture was extracted with ethyl acetate (×2)
  6. washthe organic layer was washed with saturated sodium chloride solution
  7. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  8. customthe solvent was evaporated under reduced pressure, and moisture
  9. customwas removed from the resulting residue azeotropically with toluene (×2)

Quellen und Nachweise

ORD-Eintrag
ord-37408d19d5b646c79129897c8fe5c544
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476253B2

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