WO2007096314A3 - Enzymatic resolution of racemic 3-aryl-4-aminobutyric acid - Google Patents

Enzymatic resolution of racemic 3-aryl-4-aminobutyric acid Download PDF

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Publication number
WO2007096314A3
WO2007096314A3 PCT/EP2007/051538 EP2007051538W WO2007096314A3 WO 2007096314 A3 WO2007096314 A3 WO 2007096314A3 EP 2007051538 W EP2007051538 W EP 2007051538W WO 2007096314 A3 WO2007096314 A3 WO 2007096314A3
Authority
WO
WIPO (PCT)
Prior art keywords
aryl
aminobutyric acid
acid ester
racemic
pyrrolidinone
Prior art date
Application number
PCT/EP2007/051538
Other languages
French (fr)
Other versions
WO2007096314A2 (en
Inventor
Grigory Veinberg
Maksim Vorona
Antons Lebedevs
Aleksandrs Chernobrovijs
Ivars Kalvinsh
Original Assignee
Grigory Veinberg
Maksim Vorona
Antons Lebedevs
Aleksandrs Chernobrovijs
Ivars Kalvinsh
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 Grigory Veinberg, Maksim Vorona, Antons Lebedevs, Aleksandrs Chernobrovijs, Ivars Kalvinsh filed Critical Grigory Veinberg
Priority to EA200801878A priority Critical patent/EA014980B1/en
Publication of WO2007096314A2 publication Critical patent/WO2007096314A2/en
Publication of WO2007096314A3 publication Critical patent/WO2007096314A3/en

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    • 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
    • C12P13/001—Amines; Imines
    • 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
    • C12P13/02—Amides, e.g. chloramphenicol or polyamides; Imides or polyimides; Urethanes, i.e. compounds comprising N-C=O structural element or polyurethanes
    • 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
    • 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
    • C12P41/006—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by reactions involving C-N bonds, e.g. nitriles, amides, hydantoins, carbamates, lactames, transamination reactions, or keto group formation from racemic mixtures

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

Abstract

A process for the enzymatic resolution of racemic 3-aryl-4-aminobutyric acid ester into its R-and S-enantiomers, wherein aryl is represented by phenyl group (Phenybut) or p-chlorophenyl group (Baclofen) and ester group by saturated or unsaturated alkyl containing from 2 to 8 carbon atoms. The disclosed process includes the following steps: (1) selective cyclization of 3(S)-aryl-4-aminobutyric acid ester into 4(S)-aryl-2-pyrrolidinone using racemic 3-aryl-4-aminobutyric acid ester in water solution in the presence of -chymotrypsin; (2) acidification of reaction mixture to pH<2.0 and separation of 4(S)-aryl-2-pyrrolidinone and 3(R)-aryl-4-aminobutyric acid ester by extraction; (3) isolation of 4(S)-aryl-2-pyrrolidinone from organic phase and 3(R)-aryl-4-aminobutyric acid ester from water phase and their conversion into respectively R-and S-isomers of 3-aryl-4-aminobutyric acid by acidic hydrolysis.
PCT/EP2007/051538 2006-02-23 2007-02-18 Enzymatic resolution of racemic 3-aryl-4-aminobutyric acid WO2007096314A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EA200801878A EA014980B1 (en) 2006-02-23 2007-02-18 A process for enzymatic resolution of racemic 3-aryl-4-aminobutyric acid

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
LV060028A LV13635B (en) 2006-02-23 2006-02-23 Enzymatic resolution of racemic 3-aryl-4-aminobutyric acids
LVP-06-28 2006-02-23

Publications (2)

Publication Number Publication Date
WO2007096314A2 WO2007096314A2 (en) 2007-08-30
WO2007096314A3 true WO2007096314A3 (en) 2007-11-01

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2007/051538 WO2007096314A2 (en) 2006-02-23 2007-02-18 Enzymatic resolution of racemic 3-aryl-4-aminobutyric acid

Country Status (3)

Country Link
EA (1) EA014980B1 (en)
LV (1) LV13635B (en)
WO (1) WO2007096314A2 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5380743B2 (en) * 2008-06-19 2014-01-08 住友化学株式会社 Process for producing optically active 4-amino-3-substituted phenylbutanoic acid
LV15015B (en) 2013-12-13 2015-12-20 Olainfarm, A/S Salt of 3-carboxy-4-(r)-phenylpyrrolidinone-2 and uses thereof
FR3054218B1 (en) * 2016-07-22 2020-03-06 Universite De Rouen PROCESS FOR SPLITTING BACLOFENE SALTS
CN115282928B (en) * 2022-08-04 2023-08-15 杭州佳嘉乐生物技术有限公司 Novel separation medium and application thereof

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997022578A1 (en) * 1995-12-20 1997-06-26 Farmarc Nederland B.V. A process for the optical resolution of 3-(p-chlorophenyl)-glutaramide
US5843765A (en) * 1997-01-31 1998-12-01 National Research Council Of Canada Streptomyces microorganism useful for the preparation of (R)-baclofen from the racemic mixture

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997022578A1 (en) * 1995-12-20 1997-06-26 Farmarc Nederland B.V. A process for the optical resolution of 3-(p-chlorophenyl)-glutaramide
US5843765A (en) * 1997-01-31 1998-12-01 National Research Council Of Canada Streptomyces microorganism useful for the preparation of (R)-baclofen from the racemic mixture

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
CHENEVERT R ET AL: "CHEMOENZYMATIC ENANTIOSELECTIVE SYNTHESIS OF BACLOFEN", CANADIAN JOURNAL OF CHEMISTRY, vol. 72, no. 11, 1 November 1994 (1994-11-01), pages 2312 - 2317, XP000644775, ISSN: 0008-4042 *
CHENEVERT R ET AL: "CHEMOENZYMATIC SYNTHESIS OF BOTH ENANTIOMERS OF BACLOFEN", TETRAHEDRON LETTERS, vol. 32, no. 34, 1991, pages 4249 - 4250, XP002448302, ISSN: 0040-4039 *
FELLUGA F ET AL: "A short and convenient chemoenzymatic synthesis of both enantiomers of 3-phenylGABA and 3-(4-chlorophenyl)GABA (Baclofen)", TETRAHEDRON: ASYMMETRY, vol. 16, no. 7, 4 April 2005 (2005-04-04), pages 1341 - 1345, XP004807198, ISSN: 0957-4166 *

Also Published As

Publication number Publication date
LV13635B (en) 2008-01-20
EA014980B1 (en) 2011-04-29
EA200801878A1 (en) 2009-04-28
WO2007096314A2 (en) 2007-08-30

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