Reaktion #169945

Reaktionsgleichung

mixture

N-[(2Z)-5-tert-butyl-3-[(2S)-tetrahydrofuran-2-ylmethyl]-1,3-thiazol-2(3H)-ylidene]-2-fluoro-5-(trifluoromethyl)benzamide

(R)-tert-butyl 2-{[tert-butyl(dimethyl)silyl]oxy}-1-(hydroxymethyl)ethylcarbamate

potassium tert-butoxide

→

title compound

Ausbeute 69.8%

tert-butyl (1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-{[2-({[(2Z)-5-tert-butyl-3-[(2S)-tetrahydrofuran-2-ylmethyl]-1,3-thiazol-2(3H)-ylidene]amino}carbonyl)-4-(trifluoromethyl)phenoxy]methyl}ethylcarbamate

Ausbeute 69.8%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe mixture was concentrated under reduced pressure
2. 2
   Sonstigethe residue was partitioned between EtOAc and water
3. 3
   WaschenThe organic layer was washed with brine
4. 4
   Trocknendried with MgSO4
5. 5
   Einengenconcentrated under reduced pressure

Vorschrift

A mixture of Example 32B (87 mg, 0.2 mmol), (R)-tert-butyl 2-{[tert-butyl(dimethyl)silyl]oxy}-1-(hydroxymethyl)ethylcarbamate (62 mg, 0.2 mmol) and 1N potassium tert-butoxide in THF (0.2 mL, 0.2 mmol) in THF (10 mL) was stirred at room temperature for 1 hour. The mixture was concentrated under reduced pressure and the residue was partitioned between EtOAc and water. The organic layer was washed with brine, dried with MgSO4 and concentrated under reduced pressure to afford 100 mg of the title compound. MS (DCI/NH3) m/z 716 (M+H)+.

Quelle