反应详情

To a solution of 2.16 g (4.11 mM) of tert-butyl 4-(diphenoxyphosphorylmethanesulfonylaminomethyl)-piperidine-1-carboxylate in toluene (20 ml)-tetrahydro-furan (20 ml) was added 0.33 g (8.23 mM) of a 60% suspension of sodium hydride in liquid paraffin at room temperature and the mixture was stirred at the prevailing temperature for 1 hour. This reaction mixture was added to a solution of the above crude 5-thia-1,8b-diazaacenaphthylene-4-carbaldehyde in N,N-dimethylformamide (10 ml)-toluene (50 ml) at room temperature and the mixture was stirred at the prevailing temperature for 0.5 hour. This reaction mixture was poured in water and extracted with 3 portions of ethyl acetate. The organic layers were pooled and dried over MgSO4 and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (ethyl acetate to ethyl acetate/methanol : 9/1) to provide crude (E)-N-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]-2-(5-thia-1,8b-diazaacenaphthylen-4-yl)vinylsulfonamide. To this crude product was added 1 ml of concentrated hydrochloric acid, and the mixture was stirred at room temperature for 30 minutes. To this reaction mixture was added ethanol, followed by stirring, and the resulting precipitate was recovered and washed serially with ethanol and diethyl ether to provide the title compound.

1. stirringthe mixture was stirred at the prevailing temperature for 0.5 hour
2. extractionextracted with 3 portions of ethyl acetate
3. dry with materialdried over MgSO4
4. distillationthe solvent was distilled off under reduced pressure