preparation method of (s)-(+)-m-nitrobenzene sulfonate glycidyl ester_industrial additives

background and overview of the preparation method of (s)-(+)-m-nitrobenzene sulfonate glycidyl ester

(s)-(+)-m-nitrobenzene sulfonate glycidyl ester is an organic intermediate, which can be synthesized from 3-nitrobenzene sulfonyl chloride and s-glycidol or (r)-3-chloro-1 , obtained by the reaction of 2-propanediol.

preparation method of (s)-(+)-m-nitrobenzene sulfonate glycidyl ester

preparation method report 1 of (s)-(+)-m-nitrobenzene sulfonate glycidyl ester,

to a stirred solution of s-glycidol (cas no. 556-52-5, available from sigma-india) (1.67g, 22.560mmol) in dichloromethane (50ml) at 0°c was added triethyl amine (3.90 ml, 27.070 mmol) 15 min. 3-nitrobenzenesulfonyl chloride (cas no. 121-51-7, available from combi-blocks) (5.00 g, 22.560 mmol) was added to the above reaction mixture, and the reaction mixture was stirred at the same temperature for 1 hour. the resulting reaction mixture methoxypyridine was poured into water (200 ml) and extracted with dichloromethane (2 x 100 ml). the combined organic phases were dried over na2so4, filtered and concentrated under reduced pressure. the resulting crude material was triturated using n-pentane to obtain ethylene oxide-2-ylmethyl 3-nitrobenzene sulfonate ethyl ester (5.00 g, 19.305 mmol).

preparation method report 2 of (s)-(+)-m-nitrobenzene sulfonate glycidyl ester,

add 499 g of tripotassium phosphate to 1.2 liters of (r)-3-chloro-1,2-propanediol (200 g, optical purity 99.5% ee) in methylene chloride, and then stir the resulting solution reflux for 3 hours. the resulting solution was cooled to 0°c, and 201 g of triethylamine, 4 g of 4-(dimethyl)pyridine and 401 g of 3-nitrobenzenesulfonyl chloride were added to the solution. after stirring for an additional hour at room temperature, the reaction mixture was washed successively with 2.2 liters of 5% aqueous potassium carbonate solution, 2 liters of indium aqueous hydrogen chloride solution and 1 liter of water. the organic layer was dried over 50 g of anhydrous sodium sulfate and filtered. dichloromethane was evaporated under reduced pressure to give the crude product (chemical purity: 99.3%, optical purity (gc) 99.54%ee). yield: 378g, 80.5%; chemical purity: 99.2%; optical purity (gc): 99.5%ee; melting point: 64~66°c.

references

[1] [invented in china] cn201880032332.4 compounds for treating or preventing prmt5-mediated diseases

[2] [chinese invention, chinese invention authorization] cn200480044254.8 a method for preparing glycidyl magnesium carbonate derivatives