WO2019191363A3 - Expedient synthesis of oseltamivir and related compounds via direct olefin diazidation-diamidation reaction - Google Patents

Expedient synthesis of oseltamivir and related compounds via direct olefin diazidation-diamidation reaction Download PDF

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Publication number
WO2019191363A3
WO2019191363A3 PCT/US2019/024481 US2019024481W WO2019191363A3 WO 2019191363 A3 WO2019191363 A3 WO 2019191363A3 US 2019024481 W US2019024481 W US 2019024481W WO 2019191363 A3 WO2019191363 A3 WO 2019191363A3
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WO
WIPO (PCT)
Prior art keywords
oseltamivir
diazidation
diamidation
reaction
related compounds
Prior art date
Application number
PCT/US2019/024481
Other languages
French (fr)
Other versions
WO2019191363A2 (en
Inventor
Hao Xu
Hongze Li
Shoujie Shen
Chengliang Zhu
Original Assignee
Georgia State University Research Foundation, Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Georgia State University Research Foundation, Inc. filed Critical Georgia State University Research Foundation, Inc.
Publication of WO2019191363A2 publication Critical patent/WO2019191363A2/en
Publication of WO2019191363A3 publication Critical patent/WO2019191363A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/10—Preparation of carboxylic acid amides from compounds not provided for in groups C07C231/02 - C07C231/08
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/04—Formation of amino groups in compounds containing carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C247/00—Compounds containing azido groups
    • C07C247/14—Compounds containing azido groups with azido groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C269/04—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups from amines with formation of carbamate groups
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P13/00—Preparation of nitrogen-containing organic compounds
    • C12P13/008—Preparation of nitrogen-containing organic compounds containing a N-O bond, e.g. nitro (-NO2), nitroso (-NO)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Zoology (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Disclosed herein are improved methods for the preparation of oseltamivir, and intermediates useful thereto.
PCT/US2019/024481 2018-03-28 2019-03-28 Expedient synthesis of oseltamivir and related compounds via direct olefin diazidation-diamidation reaction WO2019191363A2 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US201815938204A 2018-03-28 2018-03-28
US15/938,204 2018-03-28
US15/970,478 2018-05-03
US15/970,478 US10385010B1 (en) 2018-03-28 2018-05-03 Expedient synthesis of oseltamivir and related compounds via direct olefin diazidation-diamidation reaction

Publications (2)

Publication Number Publication Date
WO2019191363A2 WO2019191363A2 (en) 2019-10-03
WO2019191363A3 true WO2019191363A3 (en) 2019-12-05

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2019/024481 WO2019191363A2 (en) 2018-03-28 2019-03-28 Expedient synthesis of oseltamivir and related compounds via direct olefin diazidation-diamidation reaction

Country Status (2)

Country Link
US (1) US10385010B1 (en)
WO (1) WO2019191363A2 (en)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1127872A1 (en) * 2000-02-22 2001-08-29 F. Hoffmann-La Roche Ag Tamiflu via Diels-Alder
WO2009078813A1 (en) * 2007-12-19 2009-06-25 Nanyang Technological University Method of forming oseltamivir and derivatives thereof
US20160222029A1 (en) * 2013-10-04 2016-08-04 Council Of Scientific And Industrial Research A process for the preparation of intermediate for the preparation of oseltamivir phosphate

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1127872A1 (en) * 2000-02-22 2001-08-29 F. Hoffmann-La Roche Ag Tamiflu via Diels-Alder
WO2009078813A1 (en) * 2007-12-19 2009-06-25 Nanyang Technological University Method of forming oseltamivir and derivatives thereof
US20160222029A1 (en) * 2013-10-04 2016-08-04 Council Of Scientific And Industrial Research A process for the preparation of intermediate for the preparation of oseltamivir phosphate

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
LI, H. ET AL.: "Enantioselective Synthesis of Oseltamivir Phosphate (Tamiflu) via the Iron-Catalyzed Stereoselective Olefin Diazidation", J. AM. CHEM. SOC., vol. 140, 24 July 2018 (2018-07-24), pages 10619 - 10626, XP055659635 *
SHIN, C. -G. ET AL.: "α,β-Unsaturated Carboxylic Acid Derivatives. XVI. Synthesis and Configuration of Diels-Alder Adducts from Ethyl 3-Nitro-2-alkenoate and 1,3-Butadiene", BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, vol. 51, no. 9, 1978, pages 2618 - 2621, XP055659630 *
SULLIVAN, B. ET AL.: "Symmetry-Based Design for the Chemoenzymatic Synthesis of Oseltamivir (Tamiflu) from Ethyl Benzoate", ANGEW. CHEM. INT. ED., vol. 48, 2009, pages 4229 - 4231, XP055659633 *

Also Published As

Publication number Publication date
US10385010B1 (en) 2019-08-20
WO2019191363A2 (en) 2019-10-03

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