Synthesis of <I>N</I>-Acyloxysuccinimides with Short Chain Fatty Acid Residues and the Reactions with Aliphatic Primary Amines in Aqueous Solution

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  • 短鎖脂肪酸残基を有する<I>N</I>-アシロキシスクシンイミドの合成及び水溶液中での脂肪族第一級アミンとの反応
  • タンサ シボウサン ザンキ オ ユウスル N アシロキシスクシンイミド ノ ゴ

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The reactions of N-hydroxysuccinimide (1) with fatty acids (2) in the presence of N, N'-dicyclohexylcarbodiimide (DCC) in dioxane gave N-acyloxysuccinimides (3) (CN=211) which were purified by fractional crystallization and silica gel column chromatography. The structures of (3) were determined by GLC-MS.<BR>The reaction of (3) (CN=28) with an aliphatic primary amine in aqueous solution was studied kinetically. N-Acylation of the amine was competitive with decomposition of (3) and its rate is expressed as follows : V=-(k1, d+k2[Amine])[(3)], where k1, d is the first order rate constant and k2 is the second order rate. The rate decreased with increasing the length of carbon chain of acid residue (CN) in (3). The slope of log k2 vs. pH plot was 1.0, indicating nucleophilic attack of the free amino group on the carbonyl carbon in (3). The rate ratio, k2/k1, d, was maximum at about pH 9. The ratio, 10-3 k2/k1, d, was larger than unity for the reaction of (3) with primary amines containing straight chains. The above observations suggest a possibility of (3) be an N-acyl reagent of amino compounds in aqueous solution.

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