تفاعل #449199

معادلة التفاعل

diisopropylethyl-amine

(2S,4S)-4-mercapto-2-[4-(4-nitrobenzyloxycarbonylmethyl)-1-piperazinyl-carbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine bis(trifluoromethanesulfonate)

4-nitrobenzyl (1R,5R,6S)-6-[(1R)-1-hydroxyethyl]-1-methyl-2-oxo-1-carbapenam-3-carboxylate

diphenylphosphoryl chloride

diisopropylethylamine

→

title compound

المردود 68.0%

4-Nitrobenzyl (1R,5S,6S)-2-{(2S,4S)-2-[4-(4-nitrobenzyloxycarbonylmethyl)-1-piperazinylcarbonyl]-pyrrolidin-4-ylthio}-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

المردود 68.0%

المذيبات

acetonitrile

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooling
2. 2
   workup.WAITto stand overnight at the same temperature
3. 3
   أخرىAt the end of this time, the solvent was removed by distillation under reduced pressure
4. 4
   workup.ADDITIONusing with a 5:1 by volume mixture of ethyl acetate and methanol as the eluent
5. 5
   workup.ADDITIONThose fractions containing the title compound
6. 6
   تركيزconcentrated by evaporation under reduced pressure

الإجراء التجريبي

290 μl of diphenylphosphoryl chloride and 245 μl of diisopropylethylamine were added dropwise, whilst ice-cooling, to a solution of 500 mg of 4-nitrobenzyl (1R,5R,6S)-6-[(1R)-1-hydroxyethyl]-1-methyl-2-oxo-1-carbapenam-3-carboxylate in 5 ml of dry acetonitrile, and the resulting mixture was stirred at the same temperature for 1 hour. 520 μl of diisopropylethyl-amine and a solution of 1.57 g of (2S,4S)-4-mercapto-2-[4-(4-nitrobenzyloxycarbonylmethyl)-1-piperazinyl-carbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine bis(trifluoromethanesulfonate) (prepared as described in Preparation 56) in 5ml of dry acetonitrile were then simultaneously added dropwise to the mixture, whilst ice-cooling, and the resulting mixture was allowed to stand overnight at the same temperature. At the end of this time, the solvent was removed by distillation under reduced pressure, and the resulting residue was subjected to column chromatography through a Lobar column (Merck, LiChroprep Si60, size B), using with a 5:1 by volume mixture of ethyl acetate and methanol as the eluent. Those fractions containing the title compound were combined and concentrated by evaporation under reduced pressure, to give 706 mg of the title compound, as a powder.

المصدر