CAS: 681260-04-8; Methyl (1R,2S)-1-Amino-2-Vinylcyclopropane-1-Carboxylate

结构式图片

相似化合物

159622-09-0 3095621-03-4 259214-58-9

物理性质

MSDS等安全信息

    上下游产品

    methanol 21H23NO3C21H23NO3 (1R,2S)-1-amino-2-vinylcyclopropane carboxylic acid methyl ester tosylate salt

    合成工艺路线路线简述

    • 159622-09-0 + 6192-52-5 = 681260-04-8 + 104-15-4
      反应条件:1.1 Solvents: Methanol; 20 Min,Rt; 4 H,40 °C; Overnight,Rt
      标题:Synthesis Of (1R,2S)-1-Amino-2-Vinylcyclopropanecarboxylic Acid Vinyl-Acca) Derivatives: Key Intermediates For The Preparation Of Inhibitors Of The Hepatitis C Virus Ns3 Protease
      作者:Beaulieu,Pierre L.; Et Al
      参考文献:Journal Of Organic Chemistry 日期:2005 卷标:70(15) 页码:5869-5879]

      259217-95-3 = 681260-04-8 + 104-15-4
      反应条件:1.1 Solvents: Methanol; 0.25 H,25 - 35 °C; 2 H,50 °C1.2 Reagents: Acetic Acid Solvents: Methanol; Ph 7.3,5 °C2.1 Solvents: Methanol; 20 Min,Rt; 4 H,40 °C; Overnight,Rt
      标题:Synthesis Of (1R,2S)-1-Amino-2-Vinylcyclopropanecarboxylic Acid Vinyl-Acca) Derivatives: Key Intermediates For The Preparation Of Inhibitors Of The Hepatitis C Virus Ns3 Protease
      作者:Beaulieu,Pierre L.; Et Al
      参考文献:Journal Of Organic Chemistry 日期:2005 卷标:70(15) 页码:5869-5879]

      213316-49-5 = 681260-04-8 + 104-15-4
      反应条件:1.1 Reagents: Sodium Hydroxide,Potassium Chloride Catalysts: Subtilisin Solvents: Acetone,Water; 91 H,Ph 8.1 - 8.3,35 - 37 °C1.2 Reagents: Hydrochloric Acid Solvents: Water; 75 H,Ph 2 - 3,Rt2.1 Solvents: Methanol; 0.25 H,25 - 35 °C; 2 H,50 °C2.2 Reagents: Acetic Acid Solvents: Methanol; Ph 7.3,5 °C3.1 Solvents: Methanol; 20 Min,Rt; 4 H,40 °C; Overnight,Rt
      标题:Synthesis Of (1R,2S)-1-Amino-2-Vinylcyclopropanecarboxylic Acid Vinyl-Acca) Derivatives: Key Intermediates For The Preparation Of Inhibitors Of The Hepatitis C Virus Ns3 Protease
      作者:Beaulieu,Pierre L.; Et Al
      参考文献:Journal Of Organic Chemistry 日期:2005 卷标:70(15) 页码:5869-5879]

      24424-99-5 + 746657-36-3 + 32634-68-7 = 681260-04-8 + 104-15-4
      反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Tetrahydrofuran,Water; 0.75 H,24 °C; 22 H,20 °C2.1 Solvents: Methanol; 0.25 H,25 - 35 °C; 2 H,50 °C2.2 Reagents: Acetic Acid Solvents: Methanol; Ph 7.3,5 °C3.1 Solvents: Methanol; 20 Min,Rt; 4 H,40 °C; Overnight,Rt
      标题:Synthesis Of (1R,2S)-1-Amino-2-Vinylcyclopropanecarboxylic Acid Vinyl-Acca) Derivatives: Key Intermediates For The Preparation Of Inhibitors Of The Hepatitis C Virus Ns3 Protease
      作者:Beaulieu,Pierre L.; Et Al
      参考文献:Journal Of Organic Chemistry 日期:2005 卷标:70(15) 页码:5869-5879]

      213316-32-6 + 32634-68-7 = 681260-04-8 + 104-15-4
      反应条件:1.1 Solvents: Ethanol; 2 H,60 °C; 6 H,60 °C -> 25 °C; 18 H,Rt2.1 Reagents: Sodium Hydroxide Solvents: Tetrahydrofuran,Water; 0.75 H,24 °C; 22 H,20 °C3.1 Solvents: Methanol; 0.25 H,25 - 35 °C; 2 H,50 °C3.2 Reagents: Acetic Acid Solvents: Methanol; Ph 7.3,5 °C4.1 Solvents: Methanol; 20 Min,Rt; 4 H,40 °C; Overnight,Rt
      标题:Synthesis Of (1R,2S)-1-Amino-2-Vinylcyclopropanecarboxylic Acid Vinyl-Acca) Derivatives: Key Intermediates For The Preparation Of Inhibitors Of The Hepatitis C Virus Ns3 Protease
      作者:Beaulieu,Pierre L.; Et Al
      参考文献:Journal Of Organic Chemistry 日期:2005 卷标:70(15) 页码:5869-5879]

      259214-57-8 = 681260-04-8 + 104-15-4
      反应条件:1.1 Reagents: Sodium Hydroxide,Potassium Chloride Catalysts: Subtilisin Solvents: Acetone,Water; 91 H,Ph 8.1 - 8.3,35 - 37 °C1.2 Reagents: Hydrochloric Acid Solvents: Water; 75 H,Ph 2 - 3,Rt2.1 Solvents: Methanol; 20 Min,Rt; 4 H,40 °C; Overnight,Rt
      标题:Synthesis Of (1R,2S)-1-Amino-2-Vinylcyclopropanecarboxylic Acid Vinyl-Acca) Derivatives: Key Intermediates For The Preparation Of Inhibitors Of The Hepatitis C Virus Ns3 Protease
      作者:Beaulieu,Pierre L.; Et Al
      参考文献:Journal Of Organic Chemistry 日期:2005 卷标:70(15) 页码:5869-5879]

      213316-49-5 = 681260-04-8 + 104-15-4
      反应条件:1.1 Solvents: Methanol; 50 °C2.1 Reagents: Sodium Hydroxide,Potassium Chloride Catalysts: Subtilisin Solvents: Acetone,Water; 91 H,Ph 8.1 - 8.3,35 - 37 °C2.2 Reagents: Hydrochloric Acid Solvents: Water; 75 H,Ph 2 - 3,Rt3.1 Solvents: Methanol; 20 Min,Rt; 4 H,40 °C; Overnight,Rt
      标题:Synthesis Of (1R,2S)-1-Amino-2-Vinylcyclopropanecarboxylic Acid Vinyl-Acca) Derivatives: Key Intermediates For The Preparation Of Inhibitors Of The Hepatitis C Virus Ns3 Protease
      作者:Beaulieu,Pierre L.; Et Al
      参考文献:Journal Of Organic Chemistry 日期:2005 卷标:70(15) 页码:5869-5879]

      24424-99-5 + 821-06-7 + 138495-05-3 = 681260-04-8 + 104-15-4
      反应条件:1.1 Reagents: Lithium Tert-Butoxide Solvents: Toluene1.2 Reagents: Hydrochloric Acid Solvents: Water; 2 H,Rt1.3 Reagents: Sodium Hydroxide Solvents: Tert-Butyl Methyl Ether,Water; Ph 12 - 131.4 Overnight,Rt; 2 H,60 °C2.1 Reagents: Sodium Hydroxide,Potassium Chloride Catalysts: Subtilisin Solvents: Acetone,Water; 91 H,Ph 8.1 - 8.3,35 - 37 °C2.2 Reagents: Hydrochloric Acid Solvents: Water; 75 H,Ph 2 - 3,Rt3.1 Solvents: Methanol; 20 Min,Rt; 4 H,40 °C; Overnight,Rt
      标题:Synthesis Of (1R,2S)-1-Amino-2-Vinylcyclopropanecarboxylic Acid Vinyl-Acca) Derivatives: Key Intermediates For The Preparation Of Inhibitors Of The Hepatitis C Virus Ns3 Protease
      作者:Beaulieu,Pierre L.; Et Al
      参考文献:Journal Of Organic Chemistry 日期:2005 卷标:70(15) 页码:5869-5879]

      24424-99-5 + 133038-44-5 + 821-06-7 = 681260-04-8 + 104-15-4
      反应条件:1.1 Reagents: Lithium Tert-Butoxide Solvents: Toluene1.2 Reagents: Hydrochloric Acid Solvents: Water; 2 H,Rt1.3 Reagents: Sodium Hydroxide Solvents: Tert-Butyl Methyl Ether,Water; Ph 12 - 131.4 Overnight,Rt; 2 H,60 °C2.1 Reagents: Sodium Hydroxide,Potassium Chloride Catalysts: Subtilisin Solvents: Acetone,Water; 91 H,Ph 8.1 - 8.3,35 - 37 °C2.2 Reagents: Hydrochloric Acid Solvents: Water; 75 H,Ph 2 - 3,Rt3.1 Solvents: Methanol; 0.25 H,25 - 35 °C; 2 H,50 °C3.2 Reagents: Acetic Acid Solvents: Methanol; Ph 7.3,5 °C4.1 Solvents: Methanol; 20 Min,Rt; 4 H,40 °C; Overnight,Rt
      标题:Synthesis Of (1R,2S)-1-Amino-2-Vinylcyclopropanecarboxylic Acid Vinyl-Acca) Derivatives: Key Intermediates For The Preparation Of Inhibitors Of The Hepatitis C Virus Ns3 Protease
      作者:Beaulieu,Pierre L.; Et Al
      参考文献:Journal Of Organic Chemistry 日期:2005 卷标:70(15) 页码:5869-5879]

      100-52-7 + 623-33-6 = 681260-04-8 + 104-15-4
      反应条件:1.1 Reagents: Triethylamine,Sodium Sulfate Solvents: Tert-Butyl Methyl Ether; 0.17 H,5 °C; 24 H,Rt2.1 Reagents: Lithium Tert-Butoxide Solvents: Toluene2.2 Reagents: Hydrochloric Acid Solvents: Water; 2 H,Rt2.3 Reagents: Sodium Hydroxide Solvents: Tert-Butyl Methyl Ether,Water; Ph 12 - 132.4 Overnight,Rt; 2 H,60 °C3.1 Reagents: Sodium Hydroxide,Potassium Chloride Catalysts: Subtilisin Solvents: Acetone,Water; 91 H,Ph 8.1 - 8.3,35 - 37 °C3.2 Reagents: Hydrochloric Acid Solvents: Water; 75 H,Ph 2 - 3,Rt4.1 Solvents: Methanol; 0.25 H,25 - 35 °C; 2 H,50 °C4.2 Reagents: Acetic Acid Solvents: Methanol; Ph 7.3,5 °C5.1 Solvents: Methanol; 20 Min,Rt; 4 H,40 °C; Overnight,Rt
      标题:Synthesis Of (1R,2S)-1-Amino-2-Vinylcyclopropanecarboxylic Acid Vinyl-Acca) Derivatives: Key Intermediates For The Preparation Of Inhibitors Of The Hepatitis C Virus Ns3 Protease
      作者:Beaulieu,Pierre L.; Et Al
      参考文献:Journal Of Organic Chemistry 日期:2005 卷标:70(15) 页码:5869-5879]

      133038-44-5 + 821-06-7 = 681260-04-8 + 104-15-4
      反应条件:1.1 Reagents: Lithium Tert-Butoxide Solvents: Toluene1.2 Reagents: Hydrochloric Acid Solvents: Water; 2 H,Rt1.3 Reagents: Sodium Hydroxide Solvents: Water2.1 Solvents: Ethanol; 2 H,60 °C; 6 H,60 °C -> 25 °C; 18 H,Rt3.1 Reagents: Sodium Hydroxide Solvents: Tetrahydrofuran,Water; 0.75 H,24 °C; 22 H,20 °C4.1 Solvents: Methanol; 0.25 H,25 - 35 °C; 2 H,50 °C4.2 Reagents: Acetic Acid Solvents: Methanol; Ph 7.3,5 °C5.1 Solvents: Methanol; 20 Min,Rt; 4 H,40 °C; Overnight,Rt
      标题:Synthesis Of (1R,2S)-1-Amino-2-Vinylcyclopropanecarboxylic Acid Vinyl-Acca) Derivatives: Key Intermediates For The Preparation Of Inhibitors Of The Hepatitis C Virus Ns3 Protease
      作者:Beaulieu,Pierre L.; Et Al
      参考文献:Journal Of Organic Chemistry 日期:2005 卷标:70(15) 页码:5869-5879
    📜Ethyl (3S)-2-(Benzhydrylideneamino)-3-(Hydroxymethyl)Pent-4-Enoate置于sodium Hydride,三乙胺体系中,用 四氢呋喃,二氯甲烷 作为反应溶剂,化学反应生成 (1R,2S)-1-氨基-2-乙烯基环丙烷甲酸甲酯
    参考文献:Catalytic Asymmetric Synthesis Of Ethyl (1R,2S)-Dehydrocoronamate
    标题:Catalytic Asymmetric Synthesis Of Ethyl (1R,2S)-Dehydrocoronamate
    摘要:A Synthesis Of (1R,2S)-Dehydrocoronamic Acid Ethyl Ester Was Developed Employing A Regio-And Enantioselective Palladium-Catalysed Nucleophilic Ring-Opening Of 3,4-Epoxy-1-Butene With A Glycine Anion Equivalent As The Key Enantiodifferentiating Step. The Desired Selectivity Was Achieved Using Trost'S Naphthyl Ligand. The Subsequent Activation Of The Free Hydroxyl Group And Ring-Closure By Intramolecular S(N)2 Reaction Gave The Desired Amino Acid Ethyl Ester. (C) 2006 Elsevier Ltd. All Rights Reserved.
    DOI:10.1016/j.Tetlet.2006.12.025

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    专利信息


    专利号:US-2010323953-A1
    优先权日:2007-01-08
    标 题:Macrocyclic hepatitis c protease inhibitors
    发明人：CAMPBELL DAVID ALAN; HEPPERLE MICHAEL E; WINN DAVID T; BETANCORT JUAN MANUEL
    权利人:PHENOMIX CORP
    摘要:The present invention provides novel macrocyclic compounds that mimic peptide substrates of the hepatitis C viral protease and inhibit the viral protease, more particularly as inhibitors of the NS3 serine protease from hepatitis C virus. Methods for synthesis of the compounds are also provided. The compounds find utility as antiviral agents directed at hepatitis C. The invention further provides methods of employing such inhibitors, alone or in combination with other therapeutic agents, to treat hepatitis C infection in a subject in need of such treatment.

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    主要参考文献

    参考标题:A Concise Synthesis Of The Hcv Protease Inhibitor Biln 2061 And Its P3 Modified Analogs
    作者:Dejun Liu,Jingchao Dong,Yunxing Yin,Rujian Ma,Yifeng Shi,Hao Wu,Shuhui Chen,Ge Li |发布日期:2011.7
    摘要:A Concise Synthesis Of Biln 2061 Was Achieved Through More Efficient Installation Of P2 4‐quinoline Moiety Via Sn2 Displacement Of The β‐obs Group Located On The 4‐hydroxyl Proline Intermediate, Which Was Prepared From 4‐α‐hydroxyl Proline Analog Via Mitsunobu Reaction With Inversion Of Stereochemistry. In Addition, A Short And Practical Synthesis For P3 Unit Is Also Described Herein. Final Assembly

    合成参考文献


    参考文献:10.1055/s-0040-1705870
    摘要:Synthesis of BI 201420. Synfacts. 2020 Aug 18;16(09):1009. doi: 10.1055/s-0040-1705870.
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