Reaktion #168155

Reaktionsgleichung

NaNO2

3-[(S)-1-(3′,4′-diamino-biphenyl-4-yl)-ethyl]-(S)-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-[1,3]oxazinan-2-one

→

title compound

3-{(S)-1-[4-(3H-Benzotriazol-5-yl)-phenyl]-ethyl}-(S)-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-[1,3]oxazinan-2-one

Lösungsmittel

water

acetic acid

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe resulting mixture is extracted with ethyl acetate
2. 2
   WaschenThe combined organic extracts were washed with saturated aqueous NaHCO3 solution, water, and brine
3. 3
   Trocknendried (Na2SO4)
4. 4
   SonstigeThe solvent was removed
5. 5
   Sonstigethe residue was purified by chromatography on silica gel (ethyl acetate/MeOH 98:2→80:20)

Vorschrift

A solution of NaNO2 (0.16 g) in water (2 mL) was added dropwise to an ice-cold solution of 3-[(S)-1-(3′,4′-diamino-biphenyl-4-yl)-ethyl]-(S)-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-[1,3]oxazinan-2-one (0.43 g) in acetic acid (10 mL). The resulting mixture was stirred with cooling for 2 h and at room temperature for another 1 h. Then, water (100 mL) was added and the resulting mixture is extracted with ethyl acetate. The combined organic extracts were washed with saturated aqueous NaHCO3 solution, water, and brine and dried (Na2SO4). The solvent was removed and the residue was purified by chromatography on silica gel (ethyl acetate/MeOH 98:2→80:20) to afford the title compound as a foam-like solid.

Quelle