WO2023161204A1 - Procédé de production d'esters d'acide cis-4-aminotétrahydrofuran-2-carboxylique - Google Patents

Procédé de production d'esters d'acide cis-4-aminotétrahydrofuran-2-carboxylique Download PDF

Info

Publication number
WO2023161204A1
WO2023161204A1 PCT/EP2023/054258 EP2023054258W WO2023161204A1 WO 2023161204 A1 WO2023161204 A1 WO 2023161204A1 EP 2023054258 W EP2023054258 W EP 2023054258W WO 2023161204 A1 WO2023161204 A1 WO 2023161204A1
Authority
WO
WIPO (PCT)
Prior art keywords
compounds
aminotetrahydrofuran
carboxylic acid
general formula
salt
Prior art date
Application number
PCT/EP2023/054258
Other languages
German (de)
English (en)
Inventor
Dirk Brohm
Andreas REMBIAK
Wahed Ahmed Moradi
Original Assignee
Bayer Aktiengesellschaft
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 Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Publication of WO2023161204A1 publication Critical patent/WO2023161204A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Definitions

  • the present invention relates to a new process for preparing the salts of cis-4-aminotetrahydrofuran-2-carboxylic acid esters of general formula (I).
  • the object of the present invention is to find a process for preparing cis-4-aminotetrahydrofuran-2-carboxylic acid esters which is inexpensive and can be used on an industrial scale. It is also desirable to obtain these compounds in an environmentally friendly manner, in high yield and in high purity, so that they do not have to be subjected to any further complex purification, as a result of which the corresponding crop protection agents can then also be produced on an industrial scale.
  • an acid is added to the reaction mixture.
  • R 1 is (C i -Cg)alkyl.
  • radical definitions for the compounds of the general formulas (I) and (II) are the following:
  • R1 represents CH3.
  • the compounds of formula (II) in the form of a salt react in the presence of hydrogen, a rhodium catalyst in a solvent to give compounds of the general formula (I) in the form of a salt.
  • the pressure during the reaction is from 1 to 100 bar, preferably from 5 to 50 bar, particularly preferably from 20 to 50 bar.
  • the temperature during the reaction is 0°C to 100°C, preferably 10°C to 80°C, particularly preferably 20 to 40°C.
  • rhodium catalysts or mixed catalysts consisting of rhodium and one or more other metals can be used as catalysts, for example: Rh/C, Rh/Alox, Rh+Pd/C, Rh+Pt/C, Rh+Cu/C , Rh+Ru/C; preferred: Rh/C, Rh+Pd/C, Rh/Alox; particularly preferred: Rh/C, Rh/Alox.
  • the catalysts are used with a precious metal loading of 0.5-10% precious metal on the carrier material; 1-5% noble metal is preferably applied to the carrier material.
  • the catalysts are used in an amount of 0.1-10% by weight, based on the compounds of the formula (II); 0.5-5% by weight are preferably used.
  • the amount of catalyst used is calculated based on the dry mass of the catalyst.
  • the catalysts can be used dry or wet with water.
  • Water-moist catalysts can be washed with dry solvent under an inert gas atmosphere before the reaction in order to remove adhering water.
  • the water can be removed by azeotropic distillation with a suitable solvent. Toluene, for example, can be used for the azeotropic distillation.
  • the catalyst can be reused or used once or, preferably, several times. Reactivation of the catalyst, for example by suitable washing, can be advantageous for its reuse, for example by washing with methanol or acidic methanol.
  • the compounds of the formula (II) are used as salts, optionally with an acid. Another acid or an acid mixture can also be added to the reaction mixture.
  • the following acids are preferably used for salt formation with compounds of the formula (II) and/or as an additive: HCl, H2SO4, MsOH, TfOH, TFA. HCl is particularly preferred.
  • the molar ratio of the acid to the compound of formula (II) is 0-100%, preferably 0-10%.
  • Suitable solvents and solvent mixtures are e.g.: R'OH. R ⁇ H/toluene, preferred is R'OH.
  • the salt-free form can be obtained by treating the salt with a base, for example triethylamine.
  • the products were characterized by 'H-NMR spectroscopy and/or GC/MS (Gas Chromatography Mass Spectrometry).
  • the NMR spectra were measured with a Bruker AV III 600.
  • the GC/MS samples were measured with a Shimadzu GCMS-QP-2010-Ultra coupled with an additional FID (Flame Ionization Detector). For this purpose, the samples were first evaporated and then 1-10 mg of dry sample were mixed with 250 ⁇ l of N-methyl-N-trimethylsilyltrifluoroacetamide for silylation. After a reaction time of 1-5 minutes, the samples were diluted with 1 ml acetonitrile and measured.
  • FID Fluor Ionization Detector
  • the quantitative GC determinations were measured on a GC Agilent HB7890 B series.
  • the technique is based on GC with FID detection, an RTX-5 amine column and with internal standard evaluation (internal standard: diethyl phthalate).
  • the samples, reference standard and internal standard are dissolved in methanol.

Abstract

L'invention concerne un nouveau procédé de production de sels d'esters d'acide cis-4-aminotétrahydrofuran-2-carboxylique de formule générale (I).
PCT/EP2023/054258 2022-02-24 2023-02-21 Procédé de production d'esters d'acide cis-4-aminotétrahydrofuran-2-carboxylique WO2023161204A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP22158629.0 2022-02-24
EP22158629 2022-02-24

Publications (1)

Publication Number Publication Date
WO2023161204A1 true WO2023161204A1 (fr) 2023-08-31

Family

ID=80461327

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2023/054258 WO2023161204A1 (fr) 2022-02-24 2023-02-21 Procédé de production d'esters d'acide cis-4-aminotétrahydrofuran-2-carboxylique

Country Status (2)

Country Link
TW (1) TW202400568A (fr)
WO (1) WO2023161204A1 (fr)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012130798A1 (fr) 2011-03-31 2012-10-04 Bayer Cropscience Ag 3-phénylisoxazolino-5-carboxamides et 3-phénylisoxazolino-5-thioamides à activité herbicide et fongicide
WO2016145082A1 (fr) * 2015-03-09 2016-09-15 Northwestern University Inactivateurs de la gaba aminotransférase à base de tétrahydrothiophène
WO2019001420A1 (fr) * 2017-06-27 2019-01-03 Janssen Pharmaceutica Nv Dérivés hétéroaryldihydropyrimidine et méthodes de traitement d'infections par le virus de l'hépatite b
WO2021170464A1 (fr) 2020-02-28 2021-09-02 Basf Se Malonamides herbicides
WO2022018057A1 (fr) 2020-07-23 2022-01-27 Bayer Aktiengesellschaft Procédé de préparation d'aminofurannes

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012130798A1 (fr) 2011-03-31 2012-10-04 Bayer Cropscience Ag 3-phénylisoxazolino-5-carboxamides et 3-phénylisoxazolino-5-thioamides à activité herbicide et fongicide
WO2016145082A1 (fr) * 2015-03-09 2016-09-15 Northwestern University Inactivateurs de la gaba aminotransférase à base de tétrahydrothiophène
WO2019001420A1 (fr) * 2017-06-27 2019-01-03 Janssen Pharmaceutica Nv Dérivés hétéroaryldihydropyrimidine et méthodes de traitement d'infections par le virus de l'hépatite b
WO2021170464A1 (fr) 2020-02-28 2021-09-02 Basf Se Malonamides herbicides
WO2022018057A1 (fr) 2020-07-23 2022-01-27 Bayer Aktiengesellschaft Procédé de préparation d'aminofurannes

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
CAS, no. 1170719-58-0
DANIEL WALKER ET AL: "Synthesis of ( )-8-Oxa-3-azabicyclo[3.2.1]octan-2-thione and ( )-2-Oxa-5-azabicyclo[2.2.1]heptan-6-thione: Potential Synthons for the Preparation of Novel Heteroaryl-Annulated Bicyclic Morpholines", SYNTHESIS, vol. 2011, no. 07, 8 March 2011 (2011-03-08), STUTTGART, DE., pages 1113 - 1119, XP055283027, ISSN: 0039-7881, DOI: 10.1055/s-0030-1258464 *
WALKER ET AL., SYNTHESIS, vol. 7, 2011, pages 1113 - 1119
WOLTER ET AL., ORG. LETT., vol. 11, 2009, pages 2804

Also Published As

Publication number Publication date
TW202400568A (zh) 2024-01-01

Similar Documents

Publication Publication Date Title
DE3002678C2 (fr)
EP2393817B1 (fr) Procédé pour préparer de la 2,6-dioxabicyclo-(3.3.0)-octan-4,8-dione
EP0099516A1 (fr) Procédé pour la préparation de bis(aminocyclohexyl)dialkylméthanes
EP0099981B1 (fr) Procédé de préparation de l'acide glyoxylique et de dérivés de l'acide glyoxylique
DE2418499C2 (de) Verfahren zur Herstellung von α-6-Desoxytetracyclin
AT390253B (de) Verfahren zur herstellung der d-2-(6-methoxy-2naphthyl)-propionsaeure
DE112016003289T5 (de) Verfahren zur herstellung einer 4-(trifluormethylsulfonyl)phenol-verbindung
WO2023161204A1 (fr) Procédé de production d'esters d'acide cis-4-aminotétrahydrofuran-2-carboxylique
DE2308252A1 (de) Verfahren zur herstellung von mesotetraarylporphinen
EP0089417B1 (fr) Procédé pour la préparation du phtalide
DE602005004834T2 (de) Ein verbessertes Verfahren für die Synthese von Methylphenidaten und Zwischenprodukten
DE4138142C2 (de) Verfahren zur Herstellung von 1-Amino-2,6-dimethylpiperidin
DE2455238A1 (de) Verfahren zur herstellung aromatischer hydroxylamine durch hydrierung aromatischer nitroderivate
WO2023186692A1 (fr) Procédé de production d'esters d'acide cis-4-aminotétrahydrofuran-2-carboxylique
EP0422366B1 (fr) Procédé pour la préparation de pyrolidin-2-ones N-substitués
EP0028375B1 (fr) Procédé de préparation de l'acide phénylacétique et de ses dérivés simples
AT390947B (de) Verfahren zur herstellung von diphenylessigsaeuredimethylamid
DE2804263A1 (de) Verfahren zur herstellung von indolin-derivaten
EP0936220A1 (fr) Procédé pour la préparation catalytique des 3-isochromanones commencant des phthalanes
CH678527A5 (en) Trans(E)-N-(1-naphthyl:methyl)-heptenyl-amine prepn. - by simultaneously converting crude mixt. contg. cis and trans isomers to salt and precipitating trans isomer
DE2656765A1 (de) Verfahren zur reduktion von 4-oxopiperidinen zu 4-hydroxypiperidinen
DE60204473T2 (de) VERFAHREN ZUR HERSTELLUNG VON 4-(HYDROXY)-ç1,4-!BIPIPERIDINYL-L-CARBONSÄURE-TERT.-BUTYLESTER
DE60126298T2 (de) 4,8-dodecadiendinitril und verfahren zu dessen herstellung
DE60100523T2 (de) Verfahren zur Herstellung von N-carboxy-t-leucin Anhydrid
WO1999062895A1 (fr) Procede de preparation de butyrolactones

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 23705428

Country of ref document: EP

Kind code of ref document: A1