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有机化学
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有机化学 ›› 2006, Vol. 26 ›› Issue (07): 971-974. 上一篇    下一篇

研究简报

一步法合成N-1,3-二羟基丙烷-2-基烷基乙酰胺

李家明1，汪志勇*,1，曾雷2，周明明*,2   

  1. (1中国科学技术大学化学系 合肥 230026)
    (2 Department of Physiology and Biophysics, Mount Sinai School of Medicine, New York 10029, USA)
  • 收稿日期:2005-08-25 修回日期:2006-01-10 发布日期:2006-07-01
  • 通讯作者: 周明明

One-Pot Synthesis of N-1,3-Dihydroxyprop-2-ylalkylacetamide

LI Jia-Ming1,WANG Zhi-Yong*,1,ZENG Lei2,ZHOU Ming-Ming*,2   

  1. (1 Department of Chemistry, University of Science and Technology of China, Hefei 230026, China)
    (2 Department of Physiology and Biophysics, Mount Sinai School of Medicine, New York 10029, USA)
  • Received:2005-08-25 Revised:2006-01-10 Published:2006-07-01
  • Contact: ZHOU Ming-Ming

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以5-氨基烷基-2,2-二甲基-1,3-二噁烷为起始原料, 乙酸酐为酰化剂, 一步法选择性地合成氨基二醇类氨基乙酰化产物N-1,3-二羟基丙烷-2-基烷基乙酰胺. 该方法操作简便, 收率高. 所合成的4个新化合物的结构均经FTIR, 1H NMR, 13C NMR及HRMS确证. N-3-(1,3-二羟基丙烷-2-基)丙基乙酰胺(1a)作为关键的中间体, 可以用于HIV-1 Tat/ PCAF BRD抑制剂4的合成.

关键词: 乙酸酐, 选择性乙酰化, 一步法合成, N-1,3-二羟基丙烷-2-基烷基乙酰胺

One-pot synthesis of N-1,3-dihydroxyprop-2-ylalkylacetamide was realized by the reaction of 5-amino-2, 2-dimethyl-1,3-dioxane with acetic anhydride in high regioselectivity and yield with easiness for operation under mild condition. The structures of the products were identified with FTIR, 1H NMR, 13C NMR and HRMS spectra. Compound 4, which should be a potential inhibitor of HIV-1 Tat/PCAF BRD association, can be synthesized from N-3-(1,3-dihydroxyprop-2-yl)propylacetamide easily.

Key words: acetic anhydride, highly selective acylation, one-pot synthesis, N-1,3-dihydroxyprop-2-ylalkylacetamide