反应详情

To a liquid mixture of a solution of (2S,4R)-N-t-butoxycarbonyl-4-t-butyldimethylsiloxy-2-mesyloxymethylpyrrolidine (5.02 g, 12.3 mmol) and p-mercaptobenzenesulfonamide (2.39 g, 12.6 mmol) in THF (60 ml) with -N,N-dimethylformamide (20 ml), 1,8-diazabicyclo[5.4.0]-7-undecene (2.46 ml, 16.4 ml) was added dropwise in a nitrogen stream at room temperature. The reaction solution was stirred at the same temperature for 7 hours and then poured into a liquid mixture of ethyl acetate with water. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and then concentrated in vacuo. The resulting residue was subjected to silica gel column chromatography (Wakogel™ C-300 heptane-ethyl acetate 9:1→4:1→3:2) to give (2S,4R)-N-t-butoxycarbonyl-4-t-butyldimethylsiloxy-2-(4-sulfamoylphenyl)thiomethylpyrrolidine (2.65 g, yield: 43.1%) as a colorless oily substance.

1. additionwas added dropwise in a nitrogen stream at room temperature
2. washThe organic layer was washed with saturated aqueous sodium chloride
3. dry with materialdried over anhydrous sodium sulfate
4. concentrationconcentrated in vacuo