Diisopropylethylamine → HCID 56991637, compound

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere at -20 ° C., to a solution of p-nitrobenzyl (1R,5S,6S)-2-diphenoxyphosphoryloxy-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate (13.76 g, 23.1 mmol) in acetonitrile (150 ml) was added N,N-diisopropylethylamine (13.44 ml, 77.1 mmol), followed by a suspension of (2S,4S)-2-(N-ethylpyrrolidin-3-yl)-4-mercaptopyrrolidine dihydrochloride (7.0 g, 25.7 mmol, compound of Reference Example 40 in N,N-dimethylformamide (40 ml). After stirring overnight at -20° C., the reaction mixture was concentrated in vacuo. The resulting precipitate was collected by filtration, and washed with acetonitrile (30 ml) followed by isopropyl ether (30 ml) to obtain p-nitrobenzyl (1R,5S,6S)-2-[(2S, 4S)-2-(N-ethylpyrrolidin-3-yl)pyrrolidin-4-ylthio]-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate (10.1 g, yield: 72%) as a crude crystal.

Provenance & Evidence