N-[(1-cyanoazetidin-3-yl)methyl]benzenesulfonamide

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Following general procedure 11, to a cold (0° C.), stirred solution of the amine (48) (100 mg, 1 equiv.) and Et3N (0.12 mL, 1.5 equiv.) in CH2Cl2 (5 mL) was added benzenesulfonyl chloride (0.08 mL, 1.1 equiv.). The resultant mixture was stirred at rt for 16 h. The mixture was then diluted with EtOAc and washed successively with 10% citric acid, H2O and brine. The organic extract was dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography (gradient elution: 30% EtOAc in hexane to 50% EtOAc in hexane) to afford the desired coupled product. The N-Boc group of the coupled product was then converted to the cyanamide (N—CN) following general procedure 3 (i.e. successive treatment with TFA and BrCN). The crude material was purified by flash chromatography (gradient elution: 30% EtOAc in hexane to 67% EtOAc in hexane) to afford the desired solid N-[(1-cyano-3-azetidinyl)methyl]benzenesulfonamide (50). washed successively with 10% citric acid, H2O and brine The organic extract was dried (MgSO4) concentrated under reduced pressure The residue was purified by flash chromatography (gradient elution: 30% EtOAc in hexane to 50% EtOAc in hexane) to afford the The crude material was purified by flash chromatography (gradient elution: 30% EtOAc in hexane to 67% EtOAc in hexane)