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Development of a mild amide-cleavage reaction

Research Project

Project/Area Number 25460012
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Chemical pharmacy
Research InstitutionKanazawa University

Principal Investigator

Yamada Kohei  金沢大学, 薬学系, 助教 (40583232)

Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2015: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2014: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2013: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywordsアミド切断 / ベンジルカチオン / ベンジル化剤 / DPT-BM / アミド切断反応 / ベンジル化
Outline of Final Research Achievements

A mild method for amide-cleavage using DPT-BM, which spontaneously releases benzyl cation species when dissolved at room temperature, was developed. Benzylation of the amide with DPT-BM and the subsequent hydrolysis of the resulting intermediate benzyl imidate salt affords the corresponding amine and benzyl ester, which can be converted by hydrogenolysis into a carboxylic acid under neutral conditions. Benzylation proceeds depending on both steric and electronic factors around the amide group. Thus, some amides have been selectively cleaved over other amides. Furthermore, intramolecular chemoselective cleavage of an amide group in the presence of an ester group was achieved.

Report

(4 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • 2013 Research-status Report
  • Research Products

    (12 results)

All 2016 2015 2014 2013

All Journal Article (1 results) (of which Peer Reviewed: 1 results) Presentation (11 results) (of which Int'l Joint Research: 3 results)

  • [Journal Article] O-Benzylation of Carboxylic Acids Using 2,4,6-Tris(benzyloxy)-1,3,5-triazine (TriBOT) under Acidic or Thermal Conditions2015

    • Author(s)
      Kohei Yamada, Saki Yoshida, Hikaru Fujita, Masanori Kitamura, and Munetaka Kunishima
    • Journal Title

      European Journal of Organic Chemistry

      Volume: 36 Issue: 36 Pages: 7997-8002

    • DOI

      10.1002/ejoc.201501172

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Presentation] トリアジノン骨格を基盤とする新規脱水縮合剤の開発2016

    • Author(s)
      古田美佳、山田耕平、藤田光、国嶋崇隆
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      横浜
    • Year and Date
      2016-03-26
    • Related Report
      2015 Annual Research Report
  • [Presentation] ポリアクリルアミドを担体とする親水性固定化脱水縮合剤の開発2016

    • Author(s)
      夏俊卿、山田耕平、国嶋崇隆
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      横浜
    • Year and Date
      2016-03-26
    • Related Report
      2015 Annual Research Report
  • [Presentation] アミド基を置換基に有するトリアジニルアンモニウム型脱水縮合剤の開発2016

    • Author(s)
      加藤大輝、矢内秀、木村円、山田耕平、北村正典、国嶋崇隆
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      横浜
    • Year and Date
      2016-03-26
    • Related Report
      2015 Annual Research Report
  • [Presentation] サイトⅠ特異的な薬物タンパク結合を検出する蛍光標識化アルブミンの開発2016

    • Author(s)
      瀧澤 祐美佳, 山田 耕平, 国嶋 崇隆
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      横浜
    • Year and Date
      2016-03-26
    • Related Report
      2015 Annual Research Report
  • [Presentation] Quick and mild methods for cleavage of amide-bonds by using a triazine-based benzylating reagent2015

    • Author(s)
      Yukiko Karuo, Kohei Yamada, Munetaka Kunishima
    • Organizer
      2015 International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Honolulu, Hawaii
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 新規酸触媒トリアジノン型ベンジル化剤の開発2015

    • Author(s)
      角山哲史、藤田光、北村正典、山田耕平、国嶋崇隆
    • Organizer
      第45回複素環化学討論会
    • Place of Presentation
      東京
    • Year and Date
      2015-11-19
    • Related Report
      2015 Annual Research Report
  • [Presentation] 薬物タンパク結合を検出する蛍光標識化アルブミンの開発2015

    • Author(s)
      巻口真穂、木野徹平、山田耕平、浅野智哉、国嶋崇隆
    • Organizer
      日本薬学会北陸支部第127回例会
    • Place of Presentation
      富山
    • Year and Date
      2015-11-15
    • Related Report
      2015 Annual Research Report
  • [Presentation] Development of acid-catalyzed alkylating reagents based on triazine chemistry2015

    • Author(s)
      Naoko Hayakawa, Kohei Yamada, Hikaru Fujita, Masanori Kitamura, Kazuma Yoshimura, Munetaka Kunishima
    • Organizer
      The 3rd International Symposium on Process Chemistry
    • Place of Presentation
      京都
    • Year and Date
      2015-07-13
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Development of a method for the synthesis of trisubstituted oxazoles by Suzuki-Miyaura Coupling2015

    • Author(s)
      Kohei Yamada, Naoto Kamimura, Hikaru Fujita, Munetaka Kunishima
    • Organizer
      the 18th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis
    • Place of Presentation
      Sitges Barcelona
    • Year and Date
      2015-06-28
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] ベンジルカチオン種の求電子付加に基づくアミド結合開裂反応の開発2014

    • Author(s)
      軽尾友紀子,山田耕平,北村正典,国嶋崇隆
    • Organizer
      創薬懇話会 2014 in 岐阜
    • Place of Presentation
      岐阜
    • Year and Date
      2014-07-09
    • Related Report
      2014 Research-status Report
  • [Presentation] ベンジルイミダートを経由するアミド結合切断反応の開発2013

    • Author(s)
      軽尾友紀子,山田耕平,北村正典,国嶋崇隆
    • Organizer
      第39回反応と合成の進歩シンポジウム
    • Place of Presentation
      福岡
    • Related Report
      2013 Research-status Report

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Published: 2014-07-25   Modified: 2019-07-29  

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