反応 #1120865

反応方程式

diisopropylethylamine

(2S,4S)-4-mercapto-2-(4-methyl-1-piperazinylcarbonyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine trifluoromethanesulfonate

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

diisopropylethylamine

diphenyl chlorophosphate

→

title compound

収率 61.2%

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

収率 61.2%

溶媒

acetonitrile

acetonitrile

反応条件

後処理

1. 1
   温度cooling
2. 2
   workup.STIRRINGthe resulting mixture was stirred at the same temperature for 2 hours
3. 3
   workup.WAITto stand overnight, whilst ice-
4. 4
   温度cooling
5. 5
   その他At the end of this time, the solvent was removed by distillation under reduced pressure
6. 6
   その他purified in a similar manner to that

実験手順

85 μl of diisopropylethylamine and 86 μl of diphenyl chlorophosphate were simultaneously added, whilst ice-cooling, to a solution of 161 mg of 4-nitrobenzyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-2-oxo-1-carbapenam-3-carboxylate in 2 ml of anhydrous acetonitrile, and the resulting mixture was stirred at the same temperature for 1 hour. At the end of this time, 232 μof diisopropylethylamine and a solution of 310 mg of (2S,4S)-4-mercapto-2-(4-methyl-1-piperazinylcarbonyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine trifluoromethanesulfonate [prepared as described in Example 1(1)] in 2 ml of anhydrous acetonitrile were 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, whilst ice-cooling. At the end of this time, the solvent was removed by distillation under reduced pressure, and the resulting residue was worked up and purified in a similar manner to that described in Example 29(1), to afford 209 mg of the title compound as a powder.

出典