CA2791879A1 - Preparation of methionine or selenomethionine from homoserine via a lactone intermediate - Google Patents

Preparation of methionine or selenomethionine from homoserine via a lactone intermediate Download PDF

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Publication number
CA2791879A1
CA2791879A1 CA2791879A CA2791879A CA2791879A1 CA 2791879 A1 CA2791879 A1 CA 2791879A1 CA 2791879 A CA2791879 A CA 2791879A CA 2791879 A CA2791879 A CA 2791879A CA 2791879 A1 CA2791879 A1 CA 2791879A1
Authority
CA
Canada
Prior art keywords
compound
formula
solvent
molar ratio
chosen
Prior art date
Legal status (The legal status 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 status listed.)
Abandoned
Application number
CA2791879A
Other languages
English (en)
French (fr)
Inventor
Stephen J. Lorbert
Kevin A. Trankler
Richard Vonder Embse
Dayna L. Turner
Tracy Rode
Cynthia K. Snoddy
James C. Peterson
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novus International Inc
Original Assignee
Novus International 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 Novus International Inc filed Critical Novus International Inc
Publication of CA2791879A1 publication Critical patent/CA2791879A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
    • C07C321/02—Thiols having mercapto groups bound to acyclic carbon atoms
    • C07C321/08—Thiols having mercapto groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C391/00—Compounds containing selenium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
    • C07D265/06—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings
    • C07D265/08—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D265/10—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with oxygen atoms directly attached to ring carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
CA2791879A 2010-03-09 2011-03-09 Preparation of methionine or selenomethionine from homoserine via a lactone intermediate Abandoned CA2791879A1 (en)

Applications Claiming Priority (9)

Application Number Priority Date Filing Date Title
US31202410P 2010-03-09 2010-03-09
US31201210P 2010-03-09 2010-03-09
US31202010P 2010-03-09 2010-03-09
US61/312,024 2010-03-09
US61/312,020 2010-03-09
US61/312,012 2010-03-09
US33391510P 2010-05-12 2010-05-12
US61/333,915 2010-05-12
PCT/US2011/027642 WO2011112649A1 (en) 2010-03-09 2011-03-09 Preparation of methionine or selenomethionine from homoserine via a lactone intermediate

Publications (1)

Publication Number Publication Date
CA2791879A1 true CA2791879A1 (en) 2011-09-15

Family

ID=44560584

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2791879A Abandoned CA2791879A1 (en) 2010-03-09 2011-03-09 Preparation of methionine or selenomethionine from homoserine via a lactone intermediate

Country Status (10)

Country Link
US (5) US8865920B2 (enExample)
EP (1) EP2545032A4 (enExample)
JP (1) JP2013522213A (enExample)
KR (1) KR20130006464A (enExample)
CN (1) CN102869646A (enExample)
BR (1) BR112012022506A2 (enExample)
CA (1) CA2791879A1 (enExample)
IN (1) IN2012KN02804A (enExample)
MX (1) MX2012010218A (enExample)
WO (2) WO2011112648A1 (enExample)

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JP2013522213A (ja) 2010-03-09 2013-06-13 ノーバス・インターナショナル・インコーポレイテッド ラクトン中間体を経由するホモセリンからのメチオニンまたはセレノメチオニンの製造
CN102558005A (zh) * 2012-01-11 2012-07-11 张家港阿拉宁生化技术有限公司 一种对环境友好的合成硒代蛋氨酸的方法
CN102898339B (zh) * 2012-10-29 2013-11-13 苏州二叶制药有限公司 一种硫普罗宁的制备方法
WO2015141886A1 (ko) * 2014-03-20 2015-09-24 씨제이제일제당(주) 미생물 유래의 o-아실호모세린으로부터 바이오 유래 호모세린락톤 염산염 및 바이오 유래 유기산을 제조하는 방법
US9834491B2 (en) 2013-03-20 2017-12-05 Cj Cheiljedang Corporation Method for producing bio-based homoserine lactone and bio-based organic acid from O-acyl homoserine produced by microorganisms
CN104356099B (zh) * 2014-11-19 2016-05-11 郑州大学 高丝氨酸内酯类化合物、其制备方法及其应用
CN104557581A (zh) * 2014-12-25 2015-04-29 吉尔生化（上海）有限公司 一种高丝氨酸的制备方法
CN105646302B (zh) * 2016-02-05 2018-01-12 宁夏紫光天化蛋氨酸有限责任公司 一种甲硫醇盐的生产方法
CN108516991A (zh) * 2018-05-28 2018-09-11 山东省农药科学研究院 一种精草铵膦的制备方法
CN108484666B (zh) * 2018-05-28 2021-02-26 山东省农药科学研究院 一种精草铵膦的合成方法
CN109535052B (zh) * 2018-12-07 2021-07-16 河南希百康健康产业有限公司 一种l-硒甲基硒代半胱氨酸的制备方法
CN109438307A (zh) * 2018-12-07 2019-03-08 济源市万洋华康生物科技有限公司 一种l-硒代蛋氨酸的制备方法
MY204363A (en) 2019-01-11 2024-08-26 Cj Cheiljedang Corp L-glufosinate intermediate and l-glufosinate preparation method
CN109796329A (zh) * 2019-03-26 2019-05-24 上海化工研究院有限公司 一种13C标记α-氨基丁酸的合成方法
CN110204517A (zh) * 2019-07-12 2019-09-06 利尔化学股份有限公司 一种(s)-(2-氧代四氢呋喃-3-基)氨基甲酸酯的制备方法
CN110683976A (zh) * 2019-11-04 2020-01-14 济源市万洋华康生物科技有限公司 一种制备(r)-硒甲基硒代半胱氨酸的方法
EP4151643A1 (en) 2021-09-16 2023-03-22 Evonik Operations GmbH Improved process for production of phosphoesters of glufosinate precursors
US20250333373A1 (en) * 2022-05-24 2025-10-30 Vulpes Agricultural Corp. L-2-Amino-4-Halobutyric Acid Derivative-L-Tartrate and Preparation Method Thereof
CN116143648A (zh) * 2022-12-05 2023-05-23 河北远大九孚生物科技有限公司 一种n-乙酰-l-苯丙氨酸的合成方法

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NL7508020A (nl) * 1974-07-09 1976-01-13 Hoechst Ag Werkwijze voor het bereiden van seleen bevattende aminozuren.
JPS539715A (en) * 1976-07-13 1978-01-28 Ajinomoto Co Inc Crystallization of dl-acetylmethionine
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KR100358922B1 (ko) 1994-08-22 2003-01-24 미쯔비시 웰 파마 가부시키가이샤 벤젠화합물및그의의약으로서의용도
DE19547236A1 (de) * 1995-12-18 1997-07-03 Degussa Verfahren zur Herstellung von D,L-Methionin oder dessen Salz
FR2750132B1 (fr) 1996-06-20 1998-08-14 Rhone Poulenc Chimie Procede d'acylation d'un ether ou thioether aromatique
JPH11236333A (ja) 1997-12-30 1999-08-31 Pfizer Prod Inc 抗ガン剤として有用なイミダゾリン−４−オン誘導体
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US20030083383A1 (en) * 1999-08-16 2003-05-01 Spallholz Julian E. Method of using synthetic L-Se-methylselenocysteine as a nutriceutical and a method of its synthesis
IN191266B (enExample) 1999-09-16 2003-10-18 Council Scient Ind Res
DK1339705T3 (da) * 2000-11-30 2006-10-09 Basf Ag Fremgangsmåde til fremstilling af liponsyre og dihydroliponsyre
FR2873376B1 (fr) * 2004-07-23 2006-11-24 Tetrahedron Sas Nouveaux seleno-hydroxyacides et leurs derives, applications en nutrition, cosmetique et pharmacie
CN1295214C (zh) * 2005-01-21 2007-01-17 山西大学 一种硒代蛋氨酸的合成方法
US7586003B2 (en) 2005-07-14 2009-09-08 Zinpro Corporation Derivatives of seleno-amino acids
DE102006004063A1 (de) 2006-01-28 2007-08-02 Degussa Gmbh Verfahren zur Herstellung von Methionin aus Homoserin
EP2054382A1 (de) * 2006-08-24 2009-05-06 Evonik Degussa GmbH Verfahren zur herstellung von d,l-2-hydroxy-4-alkylthiobuttersäuren
FR2907785B1 (fr) 2006-10-27 2009-01-16 Tetrahedron Sas Procede de preparation de l'acide 2-hydroxy-4-methylselenobutyrique, seul ou en melange avec son analogue soufre, ainsi que leurs utilisations en nutrition, en particulier en nutrition animale
EP2520645B1 (en) * 2007-04-11 2015-01-14 CJ CheilJedang Corporation Compositions and methods of producing methionine
US7906513B2 (en) * 2007-04-26 2011-03-15 Enanta Pharmaceuticals, Inc. Hydrazide-containing hepatitis C serine protease inhibitors
JP2013522213A (ja) 2010-03-09 2013-06-13 ノーバス・インターナショナル・インコーポレイテッド ラクトン中間体を経由するホモセリンからのメチオニンまたはセレノメチオニンの製造

Also Published As

Publication number Publication date
US20130211078A1 (en) 2013-08-15
US20130012728A1 (en) 2013-01-10
MX2012010218A (es) 2013-01-29
WO2011112649A1 (en) 2011-09-15
EP2545032A4 (en) 2014-01-01
US8476427B2 (en) 2013-07-02
BR112012022506A2 (pt) 2017-09-19
IN2012KN02804A (enExample) 2015-05-01
US20130006014A1 (en) 2013-01-03
CN102869646A (zh) 2013-01-09
EP2545032A1 (en) 2013-01-16
KR20130006464A (ko) 2013-01-16
US20110224458A1 (en) 2011-09-15
WO2011112648A1 (en) 2011-09-15
US8742170B2 (en) 2014-06-03
JP2013522213A (ja) 2013-06-13
US8865920B2 (en) 2014-10-21
US20110224430A1 (en) 2011-09-15

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Legal Events

Date Code Title Description
FZDE Discontinued

Effective date: 20160309