Concise and Effective New Syntheses of 8-Aminooctanoic Acid,a Precursor of Polypeptide Osmotic Accelerator
Methyl 8-chloro-6-oxooctanoate(4)was synthesized by acylating chlorination and Nenitzescu reaction from the commercial available material 6-methoxy-6-oxohexanoic acid(2).Then methyl(E)-8-(1,3-dioxoisoindolin-2-yl)-6-(2-tosylhydrazineylidene)octanoate(6)was obtained by substitution and condensation of 4.Ultimately,8-aminooctanoic acid(1)was obtained by reduction,hydrazolysis and hydrolysis reaction from 6,which was an important starting material for the synthesis of the permeation enhancer sodium N-[8-(2-hydroxybenzoyl)amino]octanoate(SNAC).The total yield of this new synthetic route was 58.9％(based on 2)with the purity of 99.83％.This new process is suitable for industrial production with mild conditions,low raw material cost and simple operations.
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