Message Board

Respected readers, authors and reviewers, you can add comments to this page on any questions about the contribution, review,        editing and publication of this journal. We will give you an answer as soon as possible. Thank you for your support!

Name
E-mail
Phone
Title
Content
Verification Code

LIU Hong-ming, QIN Ye, YAO Jian-zhong, SHENG Chun-quan, MIAO Zhen-yuan, ZHANG Wan-nian. Synthesis of N-tert-butoxycarbonyl-DL-(±)-homo-tyrosine[J]. Journal of Pharmaceutical Practice and Service, 2010, 28(5): 345-347,384.
Citation: LIU Hong-ming, QIN Ye, YAO Jian-zhong, SHENG Chun-quan, MIAO Zhen-yuan, ZHANG Wan-nian. Synthesis of N-tert-butoxycarbonyl-DL-(±)-homo-tyrosine[J]. Journal of Pharmaceutical Practice and Service, 2010, 28(5): 345-347,384.

Synthesis of N-tert-butoxycarbonyl-DL-(±)-homo-tyrosine

  • Received Date: 2010-05-02
  • Rev Recd Date: 2010-05-27
  • Objective To prepare N-tert-butoxycarbonyl-DL-(±)-homo-tyrosine(1),a key unusual amino acid and pharmaceutical intermediate for the total synthesis of novel peptides drug including cyclic or straight chain peptide. Methods Starting from L-aspartic acid(2),the target compound 1 was synthesized via 6 steps including N-methoxycarbonylation,intramolecular dehydration and anhydridation,Friedel-Crafts reaction with 2-chloroanisole,catalytic hydrogenation with 10% Pd-C,N-demethoxycarbonylation and demethylation with 48% HBr-HOAc followed by N-Butoxycarbonylation. Results Target compound 1 had been successfully synthesized in an overall yield of 49.7%.The structure of the target compound was confirmed by ESI-MS,1H NMR and 1C NMR. Conclusion The process developed has several advantages such as cheap materials,convenient workup and high yield.
  • 加载中
通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索

Article Metrics

Article views(2152) PDF downloads(917) Cited by()

Related
Proportional views

Synthesis of N-tert-butoxycarbonyl-DL-(±)-homo-tyrosine

Abstract: Objective To prepare N-tert-butoxycarbonyl-DL-(±)-homo-tyrosine(1),a key unusual amino acid and pharmaceutical intermediate for the total synthesis of novel peptides drug including cyclic or straight chain peptide. Methods Starting from L-aspartic acid(2),the target compound 1 was synthesized via 6 steps including N-methoxycarbonylation,intramolecular dehydration and anhydridation,Friedel-Crafts reaction with 2-chloroanisole,catalytic hydrogenation with 10% Pd-C,N-demethoxycarbonylation and demethylation with 48% HBr-HOAc followed by N-Butoxycarbonylation. Results Target compound 1 had been successfully synthesized in an overall yield of 49.7%.The structure of the target compound was confirmed by ESI-MS,1H NMR and 1C NMR. Conclusion The process developed has several advantages such as cheap materials,convenient workup and high yield.

LIU Hong-ming, QIN Ye, YAO Jian-zhong, SHENG Chun-quan, MIAO Zhen-yuan, ZHANG Wan-nian. Synthesis of N-tert-butoxycarbonyl-DL-(±)-homo-tyrosine[J]. Journal of Pharmaceutical Practice and Service, 2010, 28(5): 345-347,384.
Citation: LIU Hong-ming, QIN Ye, YAO Jian-zhong, SHENG Chun-quan, MIAO Zhen-yuan, ZHANG Wan-nian. Synthesis of N-tert-butoxycarbonyl-DL-(±)-homo-tyrosine[J]. Journal of Pharmaceutical Practice and Service, 2010, 28(5): 345-347,384.

Catalog

    /

    DownLoad:  Full-Size Img  PowerPoint
    Return
    Return