반응 #155416

반응 방정식

Triethylamine

Intermediate 1

(1S,4S)-4-nitrobenzyl 3-oxo-2-thia-5-azabicylco[2.2.1]heptane-5-carboxylate

(4R,5S,6S)-4nitrobenzyl 6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-3-(((3S,5S)-5-((4-sulfamoylbenzyl)carbamoyl)pyrrolidin-3-yl)thio)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

raw material 3

(4R,5S,6S)-4nitrobenzyl 6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-3-(((3S,5S)-5-((4-sulfamoylbenzyl)carbamoyl)pyrrolidin-3-yl)thio)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

ethyl acetate

→

solid

mafenide acetate

용매

dimethylformamide

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   세척The mixture was sequentially washed with water, dilute hydrochloric acid and saturated sodium bicarbonate
3. 3
   건조the organic layer was dried over anhydrous sodium sulfate
4. 4
   농축The ethyl acetate layer was concentrated
5. 5
   여과the precipitate was filtered
6. 6
   기타dried

실험 절차

Intermediate 1 and (4R,5S,6S)-4nitrobenzyl 6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-3-(((3S,5S)-5-((4-sulfamoylbenzyl)carbamoyl)pyrrolidin-3-yl)thio)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (raw material 3) (2980 g, 5.01 mol) were dissolved in dimethylformamide, and the solution was cooled to −15° C. Triethylamine was added dropwise under nitrogen protection. After the reaction is over, ethyl acetate was added. The mixture was sequentially washed with water, dilute hydrochloric acid and saturated sodium bicarbonate, and the organic layer was dried over anhydrous sodium sulfate. The ethyl acetate layer was concentrated and the precipitate was filtered, and dried to obtain 3300 g of a solid (i.e. intermediate 2) with a yield of 79.46% and a purity of 94.75%.

출처