Methanol → 2-((S)-1-tert-butoxycarbonylamino-ethyl)-3H-imidazole-4-carboxylic acid methyl ester

HRID 246556Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 246556
F[C:2](F)(F)[C:3]1[NH:7][C:6]([C@@H:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])=[N:5][CH:4]=1.[CH3:20][O-:21].[Na+].C[OH:24]>>[CH3:20][O:21][C:2]([C:3]1[NH:7][C:6]([C@@H:8]([NH:10][C:11]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:17])[CH3:9])=[N:5][CH:4]=1)=[O:24]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 71280415(S)-tert-butyl 1-(5-(trifluoromethyl)-1H-imidazol-2-yl)ethylcarbamate

Produkt 1

HCID 712803012-((S)-1-tert-butoxycarbonylamino-ethyl)-3H-imidazole-4-carboxylic acid methyl esterAusbeute 80 %

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a stirred solution of (S)-tert-butyl 1-(5-(trifluoromethyl)-1H-imidazol-2-yl)ethylcarbamate (200 mg, 716 μmol) in methanol (6 mL) was added sodium methoxide (77.4 mg, 1.43 mmol). The mixture was heated in microwave at 100° C. for 60 min. The mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate, then washed saturated aqueous sodium carbonate, brine, then dried (sodium sulfate), filtered and concentrated in vacuo to give 2-((S)-1-tert-butoxycarbonylamino-ethyl)-3H-imidazole-4-carboxylic acid methyl ester (154 mg, 80%) as a yellow solid. This was used directly in the next step without further purification. LCMS, [M+H]=270.

Aufarbeitung

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. dry with materialwashed saturated aqueous sodium carbonate, brine, then dried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ef4d6aff6a1d4377b383fbe3cd716156
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658646B2

Notizen zur Reaktion

Wird geladen…