反应详情

To a solution of (3S, 4R)-3-[(R)-1-t-butyldimethylsilyloxyethyl]-1-[1-hydroxy-1-(p-nitrobenzyloxycarbonyl)methyl]-4-[(R)-1-methyl-2-(p-nitrobenzyloxycarbonylamino)ethylthio(thiocarbonyl)]thioazetidin-2-one (12.6 g, 16.1 mmole) in tetrahydrofuran (150 ml) were added at -15° C., in turn, 2,6-lutidine (2.00 g, 18.7 mmole) and thionyl chloride (2.11 g, 17.7 mmole), and the mixture was stirred at the same temperature for 15 minutes. 2,6-Lutidine (3.45 g, 32.2 mmole) and triphenylphosphine (12.6 g, 48.1 mmole) were then added and the mixture was stirred at 65° C. under a nitrogen stream for a further 35 hours. After completion of the reaction, the reaction mixture was diluted with ethyl acetate; washed with water and dried. The solvent was distilled off under reduced pressure and the residue was purified by column chromatography (250 g of silica gel); eluted with a 15-20% v/v solution of ethyl acetate in benzene; giving the desired compound (10.9 g; 66%) in the form of a yellow oil.

1. stirringthe mixture was stirred at 65° C. under a nitrogen stream for a further 35 hours
2. customAfter completion of the reaction
3. washwashed with water
4. customdried
5. distillationThe solvent was distilled off under reduced pressure
6. customthe residue was purified by column chromatography (250 g of silica gel)
7. washeluted with a 15-20% v/v solution of ethyl acetate in benzene