Tert-butyl-(2-nitro-imidazol-1-yl)acetate → 2-(2-Nitroimidazol-1-yl)acetic acid

HRID 874719Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 874719
C([O:5][C:6](=[O:16])[CH2:7][N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[N+:13]([O-:15])=[O:14])(C)(C)C>C(O)(C(F)(F)F)=O.O.C1(SC)C=CC=CC=1>[N+:13]([C:9]1[N:8]([CH2:7][C:6]([OH:16])=[O:5])[CH:12]=[CH:11][N:10]=1)([O-:15])=[O:14]

Komponenten

5

Edukt 1

HCID 14555697Tert-butyl-(2-nitro-imidazol-1-yl)acetate

Produkt 1

HCID 3275442-(2-Nitroimidazol-1-yl)acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittelHCID 7520ThioanisoleLösungsmittel

Versuchsvorschrift

Compound 2 (2.5 g) is dissolved in 20 mL of a cocktail of TFA, water, thioanisole 95-2.5-2.5 and stirred at room temperature for one night. The mixture is then concentrated under vacuum and co-evaporated several times with diethyl ether until formation of a powder. After filtration, the precipitate is washed with dichloromethane and acetonitrile to give quantitatively the expected product. Mp 143° C. (decomposition); 1H NMR (DMSO-d6, 400 MHz) δ 5.21 (s, 2H), 7.21 (d, 1H, J=1.01 Hz), 7.64 (d, 1H, J=1.01 Hz). 13C (DMSO-d6, 101 MHz) δ 50.65, 127.69, 128.44, 168.56, 168.57; MS (ESI+/ESI−) m/z 170.12 [M−H]−, 341.05 [2M−H]−, 194.14 [M+Na]+.

Aufarbeitung

  1. concentrationThe mixture is then concentrated under vacuum
  2. filtrationAfter filtration
  3. washthe precipitate is washed with dichloromethane and acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-fe36528b0fa94110af95d795ef1a212b
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08980932B2

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