辛二酸单酯和双酯的制备Synthesisof.PDF

2007 年第 27 卷 有 机 化 学 Vol. 27, 2007 第 10 期, 1264～1267 Chinese Journal of Organic Chemistry No. 10, 1264～1267 ·研究论文· (S)-N-Boc-α-氨基庚(辛)二酸单酯和双酯的制备 缪 伟 徐卫良 张治柳 马汝建* 陈曙辉 李 革 (药明康德新药开发有限公司 上海 200131) 摘要 以(S)-N-Boc 焦谷氨酸乙酯为原料, 经 DIBAL-H 还原得到半缩醛, 然后经 Wittig 反应得到相应的烯烃, 最后氢化 制得(S)-N-Boc-α-氨基庚二酸二(单)酯, 总收率为 85.1%(二酯)和 86.1%(单酯). 另外, 以(S)-N-Boc-哌啶-2- 甲酸为原料经 酯化和氧化得内酰胺, 然后经还原、Wittig 反应、氢化得到(S)-N-Boc-α-氨基辛二酸二(单)酯, 总收率为 72.5%(二酯)和 72.4%(单酯). 产品用 1H NMR, MS 表征. 关键词 (S)-N-Boc-α-氨基庚(辛)二酸酯; (S)-N-Boc-焦谷氨酸乙酯; 合成 Synthesis of (S)-N-Boc-α-aminopimelic and (S)-N-Boc-α-amino- suberic Monoester and Diester MIAO, Wei XU, Wei-Liang ZHANG, Zhi-Liu MA, Ru-Jian* CHEN, Shu-Hui LI, Ge (WuXi PharmaTech Co., Ltd ., Shanghai 200131) Abstract A practical synthesis of (S)-N-Boc-α-aminopimelate starting from (S)-N-Boc-pyroglutamate in three steps including a reduction, a Wittig reaction and a hydrogenation with the overall yields of 85.1% (diester) and 86.1% (monoester) was developed. Meanwhile, a practical synthesis of (S)-N-Boc-α-amino- suberate starting from (S)-N-Boc-piperidine-2-carboxylic acid in five steps including an esterification, an oxygenation, a reduction, a Wittig reaction and a hydrogenation with the overall yields of 72.5% (diester) and 72.4% (monoester) was also developed. Keywords (S)-N-Boc-α-aminopimelate; (S)-N-Boc-α-aminosuberate; (S)-N-Boc