Taurine → Succinic anhydride

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2'-{[4-((2-sulfoethyl)amino)-1,4-dioxobutyl]oxy}taxol sodium salt and 2'-{[4-((3-sulfopropyl)amino-1,4-dioxobutyl]-oxy}taxol sodium salt were produced in high yield by coupling 2'-succinyltaxol with taurine (2-aminoethyl sulfonic acid) and 3-aminopropyl sulfonic acid tetrabutylammonium salts, respectively. Note that other quaternary ammonium salts may be used to make the aminoalkyl sulfonic acids organic solvent soluble. 2'-succinyltaxol was formed by the reaction of succinic anhydride with taxol for two hours at room temperature in pyridine or DMP. In comparison with the NMR spectrum of taxol, the NMR spectrum of 2'-succinyltaxol showed a downfield shift of the C-2' proton signal to 5.51 ppm, and the succinyl proton caused multiplets centered about 2.6 ppm.

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