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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 1734302Erstellt: 25. Oktober 2026

4-Toluenesulfonyl chloride → ((S)-3-(Tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-YL)methyl 4-methylbenzenesulfonate

https://huagongshe.com/reaction/1734302

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
Edukt4-Toluenesulfonyl chlorideHCID 7397—
Edukt(R)-4-Hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl esterHCID 11053464—
LösungsmittelPyridineHCID 1049—
LösungsmittelEthyl AcetateHCID 8857—
Produkt((S)-3-(Tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-YL)methyl 4-methylbenzenesulfonateHCID 1078633684,7%

Reaktionsschritte

A solution of 10.7 g of t-butyl (R)-4-hydroxymethyl-2,2-dimethyl-3-oxazolidinecarboxylate (J. Org. Chem. 52, 1987, 2361-64) in 107 ml of pyridine is treated with 9.7 g of p-toluenesulphonyl chloride. The reaction mixture is stirred for 17 hours, then taken up in ethyl acetate and washed with water. After drying and evaporation the residue is purified over silica gel with hexane/ethyl acetate (3:1). There are obtained 15.1 g of t-butyl (S)-2,2-dimethyl-4-(p-tolylsulfonyloxymethyl)-3-oxazolidinecarboxylate.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS05532232
Quelldatensatzuspto-grants-1996_07
ORD IDord-c5cead99fee5400085f7b3bcf4ae031a
Quellennotizuspto-grants-1996_07