Taurine → HCID 10399818, compound

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Reaction Steps

2,2,3,3-tetramethylcyclopropanecarbonyl taurine (TMC-taurine) is synthesized by adding tetramethylcyclopropanecarbonyl chloride (TMC-chloride) to taurine dissolved in a sodium hydroxide solution, preferably 5–15% NaOH aqueous solution, more preferably 10% NaOH aqueous solution. The reaction mixture is stirred for 3–10 hrs, preferably for 5 hr at room temperature (20–25° C.). The water is evaporated and the product is extracted by boiling ethanol. The insoluble salts are filtered off and TMC-taurine is crystallized using ethanol:diethyl ether solution. TMC-taurine is chlorinated in dry dichloromethane using thionyl chloride and the suitable amides (compound XXVII in reaction scheme II) are synthesized by slowly adding of the TMC-taurine chloride in dichloromethane to an aqueous solution of the corresponding amine (compound XXVI in reaction scheme II). After the addition, the reaction mixture is stirred for 2–5 hr, preferably for 2 hr at room temperature (20–25° C.), the organic solvent is evaporated, water is added and the products are extracted with a suitable organic medium such as chloroform. The organic fraction is dried using a drying agent such as Na2SO4 or MgSO4, filtered, evaporated and the products are crystallized using chloroform:hexane mixtures to get the desirable product. The chemical structures are identified by elemental analysis and spectroscopic methods.

Provenance & Evidence