AU2001258939A1 - Process for the preparation of enantiomerically enriched esters and alcohols - Google Patents

Process for the preparation of enantiomerically enriched esters and alcohols

Info

Publication number
AU2001258939A1
AU2001258939A1 AU2001258939A AU5893901A AU2001258939A1 AU 2001258939 A1 AU2001258939 A1 AU 2001258939A1 AU 2001258939 A AU2001258939 A AU 2001258939A AU 5893901 A AU5893901 A AU 5893901A AU 2001258939 A1 AU2001258939 A1 AU 2001258939A1
Authority
AU
Australia
Prior art keywords
acyl donor
enantiomerically enriched
preparation
secondary alcohol
residue
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
AU2001258939A
Inventor
Quirinus Bernardus Broxterman
Gerardus Karel Maria Verzijl
Johannes Gerardus Vries De
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.)
Koninklijke DSM NV
Original Assignee
DSM NV
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 DSM NV filed Critical DSM NV
Publication of AU2001258939A1 publication Critical patent/AU2001258939A1/en
Abandoned legal-status Critical Current

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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Zoology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biotechnology (AREA)
  • Analytical Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Microbiology (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (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)

Abstract

Method for the preparation of an enantiomerically enriched ester, in which a mixture of the enantiomers of the corresponding secondary alcohol is subjected, in the presence of an acyl donor, to an enantioselective conversion in the presence of a racemisation catalyst upon which the ester is formed and an acyl donor residue is obtained, and in which the acyl donor residue is irreversibly removed from the phase in which the enantioselective conversion takes place. Preferably the enantioselective conversion is carried out enzymatically and a transfer hydrogenation catalyst is used as racemisation catalyst.The secondary alcohol can be formed in situ from the corresponding ketone, in the presence of a hydrogen donor. It is also possible to use a mixture of the secondary alcohol and the corresponding ketone as substrate.Preferably the acyl donor is chosen so that the acyl donor residue is converted in situ into another compound and/or the acyl donor residue is removed via distillation under reduced pressure.The enantiomerically enriched esters obtained can subsequently be converted into the corresponding enantiomerically enriched alcohols, which are desirable intermediate products in the preparation of liquid crystals, agro chemicals or pharmaceuticals.
AU2001258939A 2000-05-26 2001-05-21 Process for the preparation of enantiomerically enriched esters and alcohols Abandoned AU2001258939A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
NL1015313 2000-05-26
NL1015313A NL1015313C2 (en) 2000-05-26 2000-05-26 Process for the preparation of enantiomerically enriched esters and alcohols.
PCT/NL2001/000383 WO2001090396A1 (en) 2000-05-26 2001-05-21 Process for the preparation of enantiomerically enriched esters and alcohols

Publications (1)

Publication Number Publication Date
AU2001258939A1 true AU2001258939A1 (en) 2001-12-03

Family

ID=19771451

Family Applications (1)

Application Number Title Priority Date Filing Date
AU2001258939A Abandoned AU2001258939A1 (en) 2000-05-26 2001-05-21 Process for the preparation of enantiomerically enriched esters and alcohols

Country Status (13)

Country Link
US (1) US6841691B2 (en)
EP (1) EP1283898B1 (en)
JP (1) JP2003533993A (en)
CN (1) CN1274839C (en)
AT (1) ATE325888T1 (en)
AU (1) AU2001258939A1 (en)
CA (1) CA2410529A1 (en)
CZ (1) CZ20023801A3 (en)
DE (1) DE60119510T2 (en)
ES (1) ES2262648T3 (en)
HU (1) HUP0302361A2 (en)
NL (1) NL1015313C2 (en)
WO (1) WO2001090396A1 (en)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2002365968A1 (en) * 2001-11-19 2003-06-10 Merck And Co., Inc. Process for the synthesis of (r)-1-(3,5-bis(trifluoromethyl)-phenyl)ethan-1-ol and esters thereof by dynamic kinetic resolution
EP1470220B1 (en) 2002-01-10 2011-10-05 Teva Pharmaceutical Industries, Ltd. Selective enzymatic esterification and solvolysis of epimeric vitamin d analog and separation of the epimers
KR100644165B1 (en) * 2002-03-14 2006-11-10 학교법인 포항공과대학교 Resolution of chiral compounds using aminocyclopentadienyl ruthenium catalysts
DE10248166A1 (en) * 2002-10-16 2004-06-17 Bayer Ag Anti-Kazlauskas lipases
WO2005014509A1 (en) * 2003-07-15 2005-02-17 Dsm Ip Assets B.V. Process for the preparation of enantiomerically enriched esters and alcohols
WO2005095629A1 (en) * 2004-03-29 2005-10-13 Dsm Ip Assets B.V. Process for the preparation of enantiomerically enriched esters and alcohols by means of azeotropically dried enzyme compositions
US20080138856A1 (en) * 2005-02-10 2008-06-12 Novozymes A/S Enzymatic Enantioselective Ester or Amide Hydrolysis or Synthesis
EP1710221A1 (en) * 2005-04-07 2006-10-11 DSM IP Assets B.V. Process for the preparation of an optically active ester
US11773118B2 (en) 2019-02-21 2023-10-03 Obi Pharma, Inc. Methods of making high enantioselective secondary alcohols

Family Cites Families (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US360622A (en) * 1887-04-05 Geoegb j
US314003A (en) * 1885-03-17 Process of purifying water
US321918A (en) * 1885-07-07 Half to feedebick g
US916637A (en) * 1907-05-20 1909-03-30 Mia Wallen Massage apparatus.
DE1208126B (en) * 1962-08-22 1965-12-30 Pulsgetriebe Erich Friedrich P Single or multiple disk overload slip clutch effective as a vibration damper
US4237920A (en) * 1979-01-29 1980-12-09 Torr Vacuum Products, Inc. Spring loaded plug valve
US4329293A (en) * 1980-10-31 1982-05-11 Fmc Corporation Trialkylamine/sulfur dioxide catalyzed sulfenylation of carbamates
MY100938A (en) 1986-06-06 1991-05-31 Ciba Geigy Ag Arylkylimidazole derivatives.
DE3879468T2 (en) 1987-09-09 1993-06-24 Merck Patent Gmbh FLUORINATED OLIGOPHENYLE AND THEIR USE IN LIQUID CRYSTALINE MATERIALS.
DE3736819A1 (en) 1987-10-30 1989-05-11 Basf Ag METHOD FOR PRODUCING 1-ARYL-ALK-1-ENEN BY DEHYDRATING 1-ARYL-ALKAN-1-OLEN WITH THE AID OF ARYL-SUBSTITUTED PHOSPHITES
DE3743824C2 (en) * 1987-12-23 1997-03-06 Hoechst Ag Process for the enzymatic resolution of racemic alcohols with / in vinyl esters by transesterification
EP0360622B1 (en) 1988-09-22 1999-07-28 Sumitomo Chemical Company Limited Novel optically active benzene derivatives, process for producing the same and liquid-crystalline composition containing said derivatives as liquid-crystalline compound and light switching elements
JP2903598B2 (en) 1990-02-13 1999-06-07 住友化学工業株式会社 Optically active aromatic carboxylic acid derivative and method for producing the same
DE4237920A1 (en) 1991-11-13 1993-05-19 Ciba Geigy Ag 3-Aryl-uracil derivs. - are effective against weeds, act as dessicants, and facilitate harvesting of cotton, potato or rape
DE4329293A1 (en) 1993-08-31 1995-03-02 Basf Ag Lipase-catalyzed acylation of alcohols with diketenes
CA2132411A1 (en) * 1994-09-19 1996-03-20 Michael Trani Enzymatic esterification of long-chain racemic acids and alcohols
US6011149A (en) 1995-03-07 2000-01-04 Novartis Ag Photochemically cross-linked polysaccharide derivatives as supports for the chromatographic separation of enantiomers
US5808056A (en) 1995-10-31 1998-09-15 Merck & Co., Inc. Process for preparing substituted azetidinones
US6184381B1 (en) 1995-12-06 2001-02-06 Japan Science & Technology Corp. Process for preparing optically active compounds
US5726172A (en) 1996-01-16 1998-03-10 Merck & Co., Inc. Tocolytic oxytocin receptor antagonists
CO4780021A1 (en) 1996-03-29 1999-05-26 Tanabe Seiyaku Co BUTADIENE DERIVATIVES AND PROCEDURE FOR THE PREPARATION OF THE SAME
US5750549A (en) 1996-10-15 1998-05-12 Merck & Co., Inc. Cycloalkyl tachykinin receptor antagonists
JPH10245889A (en) 1997-03-06 1998-09-14 Nkk Corp Thermal-deformation absorbing frame structure
NZ337698A (en) 1997-04-04 2001-07-27 Pfizer Prod Inc Nicotinamide derivatives for selective inhibition of phosphodiesterase type 4 (PDE4) and the production of tumour necrosis factor (TNF) useful for the treatment of respiratory, rheumatoid and allergic diseases
WO1999048530A1 (en) 1998-03-23 1999-09-30 Merck & Co., Inc. Combination therapy for the treatment of benign prostatic hyperplasia
JP2000010068A (en) 1998-06-23 2000-01-14 Fuji Photo Film Co Ltd Electronic equipment provided with reflection type liquid crystal display

Also Published As

Publication number Publication date
ES2262648T3 (en) 2006-12-01
WO2001090396A1 (en) 2001-11-29
DE60119510D1 (en) 2006-06-14
EP1283898B1 (en) 2006-05-10
NL1015313C2 (en) 2001-11-27
CN1274839C (en) 2006-09-13
US20040077059A1 (en) 2004-04-22
CZ20023801A3 (en) 2003-03-12
ATE325888T1 (en) 2006-06-15
HUP0302361A2 (en) 2003-10-28
DE60119510T2 (en) 2006-11-23
JP2003533993A (en) 2003-11-18
CN1430677A (en) 2003-07-16
CA2410529A1 (en) 2001-11-29
US6841691B2 (en) 2005-01-11
EP1283898A1 (en) 2003-02-19

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