反应详情

91 μl of diphenylphosphoryl chloride and 77 μl of diisopropylethylamine were added dropwise, whilst ice-cooling, to a solution of 152 mg of 4-nitrobenzyl (1R,5R,6S)-6-[(1R)-1-hydroxyethyl]-1-methyl-2-oxo-1-carbapenam-3-carboxylate in 2.0 ml of dry acetonitrile, and the resulting mixture was stirred at the same temperature for 1 hour. 176 μl of diisopropylethyl-amine and a solution of 318 mg of (2S,4S)-4-mercapto-2-[4-(2-carbamoyloxyethyl)-1-piperazinylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine trifluoromethane-sulfonate (prepared as described in Preparation 53) in 2.0 ml of dry acetonitrile were then simultaneously added dropwise to the mixture, whilst ice-cooling, and the resulting mixture was stirred at the same temperature for 2 hours, after which it was allowed to stand overnight in a refrigerator. At the end of this time, the solvent was removed by distillation under reduced pressure, and the residue was mixed with an aqueous solution of sodium hydrogencarbonate. The mixture was then extracted with ethyl acetate, and the extract was dried over anhydrous magnesium sulfate. The solvent was then removed from the extract by distillation under reduced pressure, and the resulting residue was purified by chromatography through a Lobar column (Merck, LiChroprep Si60, size B), using a 5:1 by volume mixture of ethyl acetate and methanol as the eluent to give 99 mg of the title compound, as a powder.

1. temperaturecooling
2. stirringthe resulting mixture was stirred at the same temperature for 2 hours
3. waitto stand overnight in a refrigerator
4. customAt the end of this time, the solvent was removed by distillation under reduced pressure
5. additionthe residue was mixed with an aqueous solution of sodium hydrogencarbonate
6. extractionThe mixture was then extracted with ethyl acetate
7. dry with materialthe extract was dried over anhydrous magnesium sulfate
8. customThe solvent was then removed from the
9. extractionextract by distillation under reduced pressure
10. customthe resulting residue was purified by chromatography through a Lobar column (Merck, LiChroprep Si60, size B)
11. additionby volume mixture of ethyl acetate and methanol as the eluent