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GB2387597B - Stereoselective preparation of 3-hydroxy-3-phenylpropionitrile - Google Patents

Stereoselective preparation of 3-hydroxy-3-phenylpropionitrile

Info

Publication number
GB2387597B
GB2387597B GB0317492A GB0317492A GB2387597B GB 2387597 B GB2387597 B GB 2387597B GB 0317492 A GB0317492 A GB 0317492A GB 0317492 A GB0317492 A GB 0317492A GB 2387597 B GB2387597 B GB 2387597B
Authority
GB
United Kingdom
Prior art keywords
phenylpropionitrile
hydroxy
stereoselective preparation
stereoselective
preparation
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.)
Expired - Fee Related
Application number
GB0317492A
Other versions
GB2387597A (en
GB0317492D0 (en
Inventor
Ahmed Kamal
Gollapalli Bhasker Khanna
Maddamsetty Venkateswara Rao
Kondapuram Vijaya Raghavan
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.)
Council of Scientific and Industrial Research CSIR
Original Assignee
Council of Scientific and Industrial Research CSIR
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 Council of Scientific and Industrial Research CSIR filed Critical Council of Scientific and Industrial Research CSIR
Publication of GB0317492D0 publication Critical patent/GB0317492D0/en
Publication of GB2387597A publication Critical patent/GB2387597A/en
Application granted granted Critical
Publication of GB2387597B publication Critical patent/GB2387597B/en
Anticipated expiration legal-status Critical
Expired - Fee Related 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
    • C12P13/00—Preparation of nitrogen-containing organic compounds
    • C12P13/002—Nitriles (-CN)
    • 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
    • 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)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (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)
GB0317492A 2001-01-22 2001-01-22 Stereoselective preparation of 3-hydroxy-3-phenylpropionitrile Expired - Fee Related GB2387597B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/IN2001/000008 WO2002057475A1 (en) 2001-01-22 2001-01-22 Stereoselective preparation of 3-hydroxy-3-phenylpropionitrile

Publications (3)

Publication Number Publication Date
GB0317492D0 GB0317492D0 (en) 2003-08-27
GB2387597A GB2387597A (en) 2003-10-22
GB2387597B true GB2387597B (en) 2004-11-10

Family

ID=11076298

Family Applications (1)

Application Number Title Priority Date Filing Date
GB0317492A Expired - Fee Related GB2387597B (en) 2001-01-22 2001-01-22 Stereoselective preparation of 3-hydroxy-3-phenylpropionitrile

Country Status (3)

Country Link
JP (1) JP2004520039A (en)
GB (1) GB2387597B (en)
WO (1) WO2002057475A1 (en)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8071128B2 (en) 1996-06-14 2011-12-06 Kyowa Hakko Kirin Co., Ltd. Intrabuccally rapidly disintegrating tablet and a production method of the tablets
US9358214B2 (en) 2001-10-04 2016-06-07 Adare Pharmaceuticals, Inc. Timed, sustained release systems for propranolol
DE10235206A1 (en) * 2002-08-01 2004-02-19 Basf Ag Process for the preparation of (S) -3-methylmino-1- (thien-2-yl) propan-1-ol
WO2004055194A1 (en) 2002-12-16 2004-07-01 Council Of Scientific And Industrial Research Chemoenzymatic process for stereoselective preparation of r and s enatiomers of 2-hydroxy-3-(2-thienyl) propanenitrile
US8367111B2 (en) 2002-12-31 2013-02-05 Aptalis Pharmatech, Inc. Extended release dosage forms of propranolol hydrochloride
US8545881B2 (en) 2004-04-19 2013-10-01 Eurand Pharmaceuticals, Ltd. Orally disintegrating tablets and methods of manufacture
US9884014B2 (en) 2004-10-12 2018-02-06 Adare Pharmaceuticals, Inc. Taste-masked pharmaceutical compositions
ES2409347T3 (en) 2004-10-21 2013-06-26 Aptalis Pharmatech, Inc. Pharmaceutical compositions of masked flavor with gastro-soluble porogenic agents
US7374926B2 (en) * 2004-12-23 2008-05-20 Council Of Scientific And Industrial Research Enantioconvergent chemoenzymatic synthesis of (R)-γ-amino-β-hydroxybutyric acid ((R)-GABOB)
US9161918B2 (en) 2005-05-02 2015-10-20 Adare Pharmaceuticals, Inc. Timed, pulsatile release systems
US7485754B2 (en) 2005-07-08 2009-02-03 Apotex Pharmachem Inc. Efficient method for preparing 3-aryloxy-3-arylpropylamines and their optical stereoisomers
CN102958515A (en) 2009-12-02 2013-03-06 阿普塔利斯制药有限公司 Fexofenadine microcapsules and compositions containing them
EP2348120B1 (en) * 2009-12-30 2014-06-11 Universität Wien Enzymatic reduction of 1-phenylpropanone and derivatives thereof
CN109706194B (en) * 2018-12-24 2021-04-06 浙江工业大学 A method for on-line synthesis of phenethyl alcohol β-amino alcohol derivatives based on flow chemistry enzymatic aminolysis reaction
US12162828B2 (en) * 2019-04-02 2024-12-10 Evonik Operations Gmbh Process for preparing 3-hydroxy-3-methylbutyric acid (HMB) and salts thereof
CN113219094A (en) * 2021-05-07 2021-08-06 湖北欣泽霏药业有限公司 Liquid chromatography detection method for optical isomer of tomoxetine hydrochloride oral solution
CN114058655B (en) * 2021-11-30 2023-08-29 青岛科技大学 A kind of method of enzymatic-chemical one-pot synthesis (R)-acetamidophenylpropanol

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
ITOH, TOSHIYUKI ET AL: "Enhanced enantioselectivity of enzymatic reaction by the sulfur functional group. A simple preparation of optically active.beta.- hydrox nitriles using a lipase" J. ORG. CHEM., vol.56, no. 4, 1991, pages 1521-1524, XP002179192 table II *
MASTER HOSANG E ET AL: "Highly efficient enzymatic resolution of homoallyl alcohols leading to a simple synthesis of optically pure fluoxetine and related compounds." TETRAHEDRON LETTERS, vol. 37, no.51, 1996, pages 9253-9254, XP004070613 ISSN: 0040-4039 cited in the application *
no. 15, 1989, pages 1917-1920, XP002179194 ISSN: 0040-4039 the whole document EFFENBERGER F ET AL: "ENZYME-CATALYZED REACTIONS 7.ENANTIOSELECTIVE ESTERIFICATION OF RACEMIC CYANOHYDRINS AND ENANTIOSELECTIVE HYDROLYSIS *
OR CYANOHYDRIN ESTERS BY LIPASES" LIEBIGS ANNALEN DER CHEMIE, no. 1, 1991, pages 47-54, XP002179195 ISSN: 0170-2041 schema 3 table 3 *
SAKAI T ET AL: "Lipase-Catalyzed Efficient Kinetic Resolution of 3-Hydroxy-3- (pentafluorophenyl)propionitrile" TETRAHEDRON LETTERS, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol.38, no. 11, 17 March 1997 (1997-03-17), pages 1987-1990, XP004055834 ISSN: 0040-4039 the whole document *
the whole document WANG Y-F ET AL: "LIPASE-CATALYZED IRREVERSIBLE TRANSESTERIFICATION USING ENOL ESTERS RESOLUTION OF CYANOHYDRINS AND SYNTHESES OF ETHYL-R-2-HYDROXY-4-PHENY LBUTYRATE AND S PROPRANOLOL" TETRAHEDRON LETTERS, vol. 30, *

Also Published As

Publication number Publication date
WO2002057475A1 (en) 2002-07-25
GB2387597A (en) 2003-10-22
JP2004520039A (en) 2004-07-08
GB0317492D0 (en) 2003-08-27

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Legal Events

Date Code Title Description
PCNP Patent ceased through non-payment of renewal fee

Effective date: 20120122