AR039342A1 - PROCEDURE OF ENANTIOSELECTIVE SYNTHESIS OF ELIGIBLE DERIVATIVES OF PROPARGILIC ALCOHOL CONFIGURATION R FROM ITS RACEMATS - Google Patents

PROCEDURE OF ENANTIOSELECTIVE SYNTHESIS OF ELIGIBLE DERIVATIVES OF PROPARGILIC ALCOHOL CONFIGURATION R FROM ITS RACEMATS

Info

Publication number
AR039342A1
AR039342A1 ARP030101390A AR039342A1 AR 039342 A1 AR039342 A1 AR 039342A1 AR P030101390 A ARP030101390 A AR P030101390A AR 039342 A1 AR039342 A1 AR 039342A1
Authority
AR
Argentina
Prior art keywords
alcohol
atom
compound
radical
formula
Prior art date
Application number
Other languages
Spanish (es)
Inventor
Alain Chenede
Original Assignee
Galderma Res & Dev
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 Galderma Res & Dev filed Critical Galderma Res & Dev
Publication of AR039342A1 publication Critical patent/AR039342A1/en

Links

Classifications

    • 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
    • C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
    • C12P41/003—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
    • C12P41/004—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions by esterification of alcohol- or thiol groups in the enantiomers or the inverse reaction
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
    • C07C65/19—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups having unsaturation outside the aromatic ring
    • 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
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
    • C12P7/22—Preparation of oxygen-containing organic compounds containing a hydroxy group aromatic

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Analytical Chemistry (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Procedimiento de síntesis de alcoholes quirales de configuración R con rendimiento químico elevado. Reivindicación1: Procedimiento de síntesis de compuestos orgánicos de configuración R de fórmula general (1), en la cual: R1 representa un átomo de H, un radical alquilo C1-6, un radical arilo, un átomo de halógeno, un radical -OR3, y R3 tiene la significación que se da más adelante, R2 representa un átomo de H, un radical alquilo C1-6; R3 representa un átomo de H o un radical que tiene 1 a 6 átomos de C, procedimiento caracterizado porque comprende las etapas siguientes; a) poner en contacto un compuesto de fórmula (2) con una cantidad eficaz de lipasa en presencia de un agente acilante y de un solvente para obtener una mezcla de acetato R y de alcohol S correspondientes; b) tratar la mezcla de acetato R y de alcohol S con un dialquil azodicarboxilato en presencia de trialquil- o triaril-fosfinas y de un compuesto nucleófilo, con el objeto de transformar el alcohol S en acetato R por inversión de configuración; c) obtener el alcohol R correspondiente por trans-esterificación, en presencia de metanol y de carbonato de sodio, seguida de una cristalización; y d) luego acoplar el alcohol así obtenido con el compuesto de fórmula (3), en la cual: X representa un átomo de halógeno; R1 tienen la misma significación que anteriormente; y R2' representa un átomo de H o un radical alquilo C1-6, y el éster puede eventualmente sufrir en ese último caso una reacción de saponificación para obtener el compuesto de fórmula (1) con R2 = H.Synthesis procedure of chiral alcohols of R configuration with high chemical yield. Claim 1: Synthesis process of organic compounds of R configuration of general formula (1), in which: R1 represents an H atom, a C1-6 alkyl radical, an aryl radical, a halogen atom, a -OR3 radical, and R3 has the significance given below, R2 represents an atom of H, a C1-6 alkyl radical; R3 represents an H atom or a radical having 1 to 6 C atoms, a process characterized in that it comprises the following steps; a) contacting a compound of formula (2) with an effective amount of lipase in the presence of an acylating agent and a solvent to obtain a mixture of corresponding R acetate and alcohol S; b) treating the mixture of R acetate and S alcohol with a dialkyl azodicarboxylate in the presence of trialkyl- or triaryl phosphines and a nucleophilic compound, in order to transform the alcohol S into R acetate by configuration inversion; c) obtain the corresponding R alcohol by trans-esterification, in the presence of methanol and sodium carbonate, followed by crystallization; and d) then coupling the alcohol thus obtained with the compound of formula (3), in which: X represents a halogen atom; R1 have the same significance as before; and R2 'represents an H atom or a C1-6 alkyl radical, and the ester may eventually undergo a saponification reaction to obtain the compound of formula (1) with R2 = H.

ARP030101390 2002-04-25 2003-04-23 PROCEDURE OF ENANTIOSELECTIVE SYNTHESIS OF ELIGIBLE DERIVATIVES OF PROPARGILIC ALCOHOL CONFIGURATION R FROM ITS RACEMATS AR039342A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR0205220A FR2839068B1 (en) 2002-04-25 2002-04-25 PROCESS FOR ENANTIOSELECTIVE SYNTHESIS OF ORGANIC COMPOUNDS

Publications (1)

Publication Number Publication Date
AR039342A1 true AR039342A1 (en) 2005-02-16

Family

ID=28799937

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP030101390 AR039342A1 (en) 2002-04-25 2003-04-23 PROCEDURE OF ENANTIOSELECTIVE SYNTHESIS OF ELIGIBLE DERIVATIVES OF PROPARGILIC ALCOHOL CONFIGURATION R FROM ITS RACEMATS

Country Status (2)

Country Link
AR (1) AR039342A1 (en)
FR (1) FR2839068B1 (en)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5447865A (en) * 1992-06-10 1995-09-05 Amprost Pharmaceutical, Inc. Method of resolution of hydroxy substituted cyclopentanone enantiomers using lipase and lithium salt complexation
FR2713635B1 (en) * 1993-12-15 1996-01-05 Cird Galderma New bi-aromatic propynyl compounds, pharmaceutical and cosmetic compositions containing them and uses.

Also Published As

Publication number Publication date
FR2839068B1 (en) 2006-03-10
FR2839068A1 (en) 2003-10-31

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