تفاعل #814799

معادلة التفاعل

diisopropylethylamine

(2S,4S)-4-mercapto-2-[4-(4-nitrobenzyloxycarbonyl)-1-piperazinylcarbonyl]-1-methylpyrrolidine trifluoromethanesulfonate

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

diphenylphosphoryl chloride

diisopropylethylamine

→

title compound

المردود 39.2%

4-Nitrobenzyl (1R,5S,6S)-2-[(2S,4S)-2-[4-(4-nitrobenzyloxycarbonyl)-1-piperazinylcarbonyl]-1methylpyrrolidin-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

المردود 39.2%

المذيبات

acetonitrile

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooling
2. 2
   workup.WAITto stand overnight, whilst ice-
3. 3
   درجة الحرارةcooling
4. 4
   أخرىpurified in a similar manner to that

الإجراء التجريبي

7.0 g of diphenylphosphoryl chloride and 3.4 g of diisopropylethylamine were added dropwise, whilst ice-cooling, to a solution of 8.6 g of 4-nitrobenzyl (1R,5R,6S)-6-[(1R)-1-hydroxyethyl]-1-methyl-2-oxo-1-carbapenam-3-carboxylate in 120 ml of dry acetonitrile, and the resulting mixture was stirred at the same temperature for 1 hour. 6.7 g of diisopropylethylamine and a solution of 13.8 g of (2S,4S)-4-mercapto-2-[4-(4-nitrobenzyloxycarbonyl)-1-piperazinylcarbonyl]-1-methylpyrrolidine trifluoromethanesulfonate in dry acetonitrile were then simultaneously added dropwise to the mixture, whilst ice-cooling, and the resulting mixture was allowed to stand overnight, whilst ice-cooling. At the end of this time, the reaction mixture was worked up and purified in a similar manner to that described in Example 49(a), to give 7.0 g of the title compound, as a powder.

المصدر