DK0528256T3 - D-2,4-Dihydroxy-3,3-dimethylbutanoic acid nitrile, preparation and use thereof, and process for the preparation of D-pantolactone, D-2,4-dihydroxy-3,3-dimethylbutanoic acid amide and D-pantothenic acid - Google Patents

D-2,4-Dihydroxy-3,3-dimethylbutanoic acid nitrile, preparation and use thereof, and process for the preparation of D-pantolactone, D-2,4-dihydroxy-3,3-dimethylbutanoic acid amide and D-pantothenic acid

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Publication number
DK0528256T3
DK0528256T3 DK92113262.7T DK92113262T DK0528256T3 DK 0528256 T3 DK0528256 T3 DK 0528256T3 DK 92113262 T DK92113262 T DK 92113262T DK 0528256 T3 DK0528256 T3 DK 0528256T3
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DK
Denmark
Prior art keywords
pantolactone
dihydroxy
preparation
acid
nitrile
Prior art date
Application number
DK92113262.7T
Other languages
Danish (da)
Inventor
Klaus Dr Huthmacher
Thomas Dr Beisswenger
Herbert Dr Klenk
Original Assignee
Degussa
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.)
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Publication date
Application filed by Degussa filed Critical Degussa
Application granted granted Critical
Publication of DK0528256T3 publication Critical patent/DK0528256T3/en

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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
    • C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D307/32—Oxygen atoms
    • C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/06—Preparation of carboxylic acid amides from nitriles by transformation of cyano groups into carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/11—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound oxygen atoms bound to the same saturated acyclic carbon skeleton
    • C07C255/12—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound oxygen atoms bound to the same saturated acyclic carbon skeleton containing cyano groups and hydroxy groups bound to the carbon skeleton
    • 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
    • C12P13/002—Nitriles (-CN)
    • C12P13/004—Cyanohydrins
    • 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
    • C12P13/00—Preparation of nitrogen-containing organic compounds
    • C12P13/04—Alpha- or beta- amino acids
    • C12P13/06—Alanine; Leucine; Isoleucine; Serine; Homoserine

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Health & Medical Sciences (AREA)
  • General Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Microbiology (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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

2.1. D-(-)-Pantolactone is an important intermediate in the synthesis of D-(+)-pantothenic acid or D-panthenol and can be obtained from the racemic compound by elaborate racemate resolution methods in the form of pantoic acid salts with chiral auxiliary bases and subsequent resolution of the pairs of salts with subsequent cyclisation of the pantoic acid. Since this synthesis is very elaborate, the object of the present invention is to provide a more suitable intermediate for pantolactone synthesis, which is to be obtainable straightforwardly and at low cost. 2.2. Such an intermediate is D-2,4-dihydroxy-3,3-dimethylbutyronitrile in an optical purity (D:L) of at least 80:20. D-(-)-pantolactone can be prepared in high yields by hydrolysis of the nitrile with concentrated acids. The nitrile is obtainable by reaction of hydroxypivalaldehyde with hydrogen cyanide in the presence of relatively large amounts of a D-oxynitrilase. 2.3. Preparation of D-(-)-pantolactone and D-(+)-pantothenic acid.
DK92113262.7T 1991-08-12 1992-08-04 D-2,4-Dihydroxy-3,3-dimethylbutanoic acid nitrile, preparation and use thereof, and process for the preparation of D-pantolactone, D-2,4-dihydroxy-3,3-dimethylbutanoic acid amide and D-pantothenic acid DK0528256T3 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE4126580A DE4126580A1 (en) 1991-08-12 1991-08-12 D-2,4-DIHYDROXY-3,3-DIMETHYLBUTANESAEURENITRILE, ITS PRODUCTION AND USE

Publications (1)

Publication Number Publication Date
DK0528256T3 true DK0528256T3 (en) 1996-12-02

Family

ID=6438119

Family Applications (1)

Application Number Title Priority Date Filing Date
DK92113262.7T DK0528256T3 (en) 1991-08-12 1992-08-04 D-2,4-Dihydroxy-3,3-dimethylbutanoic acid nitrile, preparation and use thereof, and process for the preparation of D-pantolactone, D-2,4-dihydroxy-3,3-dimethylbutanoic acid amide and D-pantothenic acid

Country Status (5)

Country Link
EP (1) EP0528256B1 (en)
AT (1) ATE143415T1 (en)
DE (2) DE4126580A1 (en)
DK (1) DK0528256T3 (en)
ES (1) ES2093150T3 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4322064A1 (en) * 1993-07-02 1995-01-12 Chemie Linz Deutschland Enzymatic process for the preparation of aliphatic S-cyanohydrins
RU2002114044A (en) 1999-10-29 2004-03-27 БАСФ Акциенгезельшафт (DE) L-PANTOLACTON HYDROLASE AND METHOD FOR PRODUCING D-PANTHOLACTON
EP2092060B1 (en) 2006-12-14 2014-01-22 DSM IP Assets B.V. R-hnl random variants and their use for preparing optically pure, sterically hindered cyanohydrins
EP3310768B1 (en) 2015-06-19 2020-04-15 Basf Se Preparation of pantolactone

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0172371A1 (en) * 1984-07-27 1986-02-26 F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft Process for the preparation of dehydroxypantolactone
DE3823864A1 (en) * 1988-01-29 1989-08-10 Kernforschungsanlage Juelich ENYMATIC PROCESS FOR THE PREPARATION OF OPTICALLY ACTIVE CYANHYDRINES
DE3823866A1 (en) * 1988-07-14 1990-02-15 Kernforschungsanlage Juelich Process for the preparation of S-cyanohydrins

Also Published As

Publication number Publication date
DE59207230D1 (en) 1996-10-31
EP0528256B1 (en) 1996-09-25
EP0528256A1 (en) 1993-02-24
ATE143415T1 (en) 1996-10-15
DE4126580A1 (en) 1993-02-18
ES2093150T3 (en) 1996-12-16

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