Large-Scale Practical Synthesis of Boc-Protected 4-Fluoro-l-Proline

A large-scale synthesis process of N-Boc-4-fluoro-l-proline (1) from N-Boc-4-hydroxy-l-proline methyl ester (2) using nosyl fluoride (13) as a deoxyfluorinating agent has been developed. An eco-fri...

[1]  S. Caron Where Does the Fluorine Come From? A Review on the Challenges Associated with the Synthesis of Organofluorine Compounds , 2020 .

[2]  Elizabeth Czornyj,et al.  Lessons Learned—Fluoride Exposure , 2020 .

[3]  Derek T. Ahneman,et al.  Deoxyfluorination with Sulfonyl Fluorides: Navigating Reaction Space with Machine Learning. , 2018, Journal of the American Chemical Society.

[4]  A. Doyle,et al.  PyFluor: A Low-Cost, Stable, and Selective Deoxyfluorination Reagent. , 2015, Journal of the American Chemical Society.

[5]  Hualiang Jiang,et al.  Design, synthesis and biological evaluation of 4-fluoropyrrolidine-2-carbonitrile and octahydrocyclopenta[b]pyrrole-2-carbonitrile derivatives as dipeptidyl peptidase IV inhibitors. , 2014, European journal of medicinal chemistry.

[6]  I. Greguric,et al.  Ascertaining the suitability of aryl sulfonyl fluorides for [18F]radiochemistry applications: a systematic investigation using microfluidics. , 2013, The Journal of organic chemistry.

[7]  D. VanDerveer,et al.  Synthesis of diazonium (perfluoroalkyl) benzenesulfonylimide zwitterions , 2013 .

[8]  D. K. Treiber,et al.  Novel series of pyrrolotriazine analogs as highly potent pan-Aurora kinase inhibitors. , 2011, Bioorganic & medicinal chemistry letters.

[9]  Xin Chen,et al.  Substituted 4-carboxymethylpyroglutamic acid diamides as potent and selective inhibitors of fibroblast activation protein. , 2010, Journal of medicinal chemistry.

[10]  David R. Bill,et al.  Aminodifluorosulfinium Salts: Selective Fluorination Reagents with Enhanced Thermal Stability and Ease of Handling, , 2010, The Journal of organic chemistry.

[11]  Lihe Guo,et al.  Synthesis and biological evaluation of 4-fluoroproline and 4-fluoropyrrolidine-2-acetic acid derivatives as new GABA uptake inhibitors. , 2009, Bioorganic & medicinal chemistry.

[12]  D. E. Patterson,et al.  Development of a Practical Large-Scale Synthesis of Denagliptin Tosylate , 2009 .

[13]  J. Chiba,et al.  A novel and potent VLA-4 antagonist based on trans-4-substituted cyclohexanecarboxylic acid. , 2009, Bioorganic & medicinal chemistry.

[14]  Hyunik Shin,et al.  Development of a Kilogram-Scale Synthesis of cis-LC15-0133 Tartrate, a Potent Dipeptidyl Peptidase IV Inhibitor , 2008 .

[15]  O. Repič,et al.  Practical Synthesis of a Peptide Deformylase (PDF) Inhibitor , 2008 .

[16]  K. Rangappa,et al.  Design, synthesis and structure-activity study of shorter hexa peptide analogues as HIV-1 protease inhibitors. , 2008, Bioorganic & medicinal chemistry.

[17]  Youwei Yan,et al.  Discovery of potent, selective 4-fluoroproline-based thrombin inhibitors with improved metabolic stability. , 2006, Bioorganic & medicinal chemistry.