反应详情

To a suspension of (2S,4EZ)-1-([1,1′-biphenyl]-4-ylcarbonyl)-N′-hydroxy-4-(methoxyimino)-2-pyrrolidinecarboximidamide (Intermediate 8, 170 mg, 0.48 mmol) in TMOF (20 ml), a catalytic amount of p-toluenesulfonic acid was added and the reaction mixture was heated to reflux for 16 h. TMOF was then evaporated in vacuo and the residue dissolved in DCM (15 mls). This was washed with NaHCO3(aq) (2×15 ml), dried over MgSO4 and evaporated in vacuo. Silica gel chromatography eluting with 15% EtOAc in hexanes gave the desired product, (3EZ,5S)-1-([1,1′-biphenyl]-4-ylcarbonyl)-5-(1,2,4-oxadiazol-3-yl)-3-pyrrolidinone O-methyloxime (59 mg).

1. temperaturethe reaction mixture was heated
2. temperatureto reflux for 16 h
3. customTMOF was then evaporated in vacuo
4. dissolutionthe residue dissolved in DCM (15 mls)
5. washThis was washed with NaHCO3(aq) (2×15 ml)
6. dry with materialdried over MgSO4
7. customevaporated in vacuo
8. washSilica gel chromatography eluting with 15% EtOAc in hexanes