Sodium Hydroxide → 3-({(2S)-2-[(tert-butoxycarbonyl)amino]propyl}oxy)isoxazole-5-carboxylic acid

HRID 1026207Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1026207
[OH-].[Na+].[C:3]([O:7][C:8]([NH:10][C@@H:11]([CH3:23])[CH2:12][O:13][C:14]1[CH:18]=[C:17]([C:19]([O:21]C)=[O:20])[O:16][N:15]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>C1COCC1.CO>[C:3]([O:7][C:8]([NH:10][C@@H:11]([CH3:23])[CH2:12][O:13][C:14]1[CH:18]=[C:17]([C:19]([OH:21])=[O:20])[O:16][N:15]=1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 67778409methyl 3-({(2S)-2-[(tert-butoxycarbonyl)amino]propyl}oxy)isoxazole-5-carboxylate

Produkt 1

HCID 677777153-({(2S)-2-[(tert-butoxycarbonyl)amino]propyl}oxy)isoxazole-5-carboxylic acidAusbeute 91,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

2M Aqueous sodium hydroxide solution (20 mL) was added to a solution of methyl 3-({(2S)-2-[(tert-butoxycarbonyl)amino]propyl}oxy)isoxazole-5-carboxylate (4.0 g) in THF/methanol (20 mL/20 mL), and the mixture was stirred at room temperature for 15 hr. The solvent was evaporated under reduced pressure, and the residue was neutralized with 6M hydrochloric acid and extracted with ethyl acetate. The combined organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (3.5 g).

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0002d7f6ad81411db0fb432c3da4a95d
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08729102B2

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