DE69015956D1 - Verfahren zur stereochemischen Inversion von (2S,3S)-2-Amino-3-phenyl-1,3-Propandiolen in ihre (2R,3R)-Enantiomere. - Google Patents

Verfahren zur stereochemischen Inversion von (2S,3S)-2-Amino-3-phenyl-1,3-Propandiolen in ihre (2R,3R)-Enantiomere.

Info

Publication number
DE69015956D1
DE69015956D1 DE69015956T DE69015956T DE69015956D1 DE 69015956 D1 DE69015956 D1 DE 69015956D1 DE 69015956 T DE69015956 T DE 69015956T DE 69015956 T DE69015956 T DE 69015956T DE 69015956 D1 DE69015956 D1 DE 69015956D1
Authority
DE
Germany
Prior art keywords
propanediols
enantiomers
phenyl
amino
stereochemical inversion
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 - Lifetime
Application number
DE69015956T
Other languages
English (en)
Other versions
DE69015956T2 (de
Inventor
Marco Villa
Claudio Giordano
Silvia Cavicchioli
Silvio Levi
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.)
Zambon SpA
Original Assignee
Zambon SpA
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 Zambon SpA filed Critical Zambon SpA
Application granted granted Critical
Publication of DE69015956D1 publication Critical patent/DE69015956D1/de
Publication of DE69015956T2 publication Critical patent/DE69015956T2/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/31—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C07C323/32—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to an acyclic carbon atom of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D263/06—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by oxygen atoms, attached to ring carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
DE69015956T 1989-10-20 1990-10-16 Verfahren zur stereochemischen Inversion von (2S,3S)-2-Amino-3-phenyl-1,3-Propandiolen in ihre (2R,3R)-Enantiomere. Expired - Lifetime DE69015956T2 (de)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IT02207589A IT1237798B (it) 1989-10-20 1989-10-20 Processo per l'inversione stereochimica di (2s,3s)-2-ammino-3-fenil-1 ,3-propandioli nei corrispondenti enantiomeri (2r,3r).

Publications (2)

Publication Number Publication Date
DE69015956D1 true DE69015956D1 (de) 1995-02-23
DE69015956T2 DE69015956T2 (de) 1995-06-08

Family

ID=11191106

Family Applications (1)

Application Number Title Priority Date Filing Date
DE69015956T Expired - Lifetime DE69015956T2 (de) 1989-10-20 1990-10-16 Verfahren zur stereochemischen Inversion von (2S,3S)-2-Amino-3-phenyl-1,3-Propandiolen in ihre (2R,3R)-Enantiomere.

Country Status (9)

Country Link
US (3) US5202484A (de)
EP (1) EP0423705B1 (de)
JP (1) JP2852801B2 (de)
AT (1) ATE116957T1 (de)
DE (1) DE69015956T2 (de)
DK (1) DK0423705T3 (de)
ES (1) ES2066931T3 (de)
GR (1) GR3015686T3 (de)
IT (1) IT1237798B (de)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5243056A (en) * 1983-06-02 1993-09-07 Zambon S.P.A. Intermediates for the preparation of 1-(phenyl)-1-hydroxy-2-amino-3-fluoro propane derivatives
ES2067958T3 (es) * 1990-10-25 1995-04-01 Schering Corp Procedimiento para preparar florfenicol, sus analogos y productos intermedios de la oxazolina para dicho procedimiento.
IT1249048B (it) 1991-02-21 1995-02-11 Zambon Spa Processo per la preparazione di trans-(5r)-2-ossazoline -2,4,5, trisostituite
US5352832A (en) * 1992-12-18 1994-10-04 Schering Corporation Asymmetric process for preparing florfenicol, thiamphenicol chloramphenicol and oxazoline intermediates
IT1271800B (it) * 1994-12-27 1997-06-09 Zambon Spa Processo di preparazione degli enantiomeri dell'acido 2- (2-fluoro- 4-bifenil) propionico
AU2003248217A1 (en) * 2003-04-04 2004-10-25 Shanghai Institute Of Organic Chemistry, Chinese Academy Of Sciences An amino alcohol ligand and its use in preparation of chiral proparglic tertiary alkohols and tertiary amines via enantioselective additon reaction
US7126005B2 (en) 2003-10-06 2006-10-24 Aurobindo Pharma Limited Process for preparing florfenicol
AU2006287697A1 (en) * 2005-09-07 2007-03-15 Schering-Plough Pty. Limited An improved process for preparing oxazolidine protected aminodiol compounds useful as intermediates to Florfenicol
US7975794B2 (en) * 2005-09-28 2011-07-12 Simmons, Inc. Suspension for tracked vehicles
US7518017B2 (en) 2006-02-17 2009-04-14 Idexx Laboratories Fenicol compounds and methods synthesizing 2-trifluoroacetamido-3-substituted propiophenone compounds
JP2010534667A (ja) * 2007-07-25 2010-11-11 インターベツト・インターナシヨナル・ベー・ベー オキサゾリジンおよびオキサゾリジノンアミノジオール類ならびに関連中間体を調製するためのプロセス
CN106278964B (zh) * 2016-07-31 2018-01-16 浙江润康药业有限公司 氟苯尼考的制备方法
CN108017549A (zh) * 2017-12-07 2018-05-11 南通常佑药业科技有限公司 一种1-芳基-2-氨基-1,3-丙二醇盐酸盐衍生物的制备方法

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2538763A (en) * 1949-02-12 1951-01-23 Parke Davis & Co Phenylaminopropandiols
US2483885A (en) * 1949-02-12 1949-10-04 Parke Davis & Co Nitrophenyl acyl amido alkane diols
US2699451A (en) * 1950-11-08 1955-01-11 Parke Davis & Co Process for the production of organic amino diol derivatives
US2721207A (en) * 1952-11-01 1955-10-18 Parke Davis & Co Process for the production of amino diols and intermediate products utilized in said process
US2717268A (en) * 1952-12-16 1955-09-06 Parke Davis & Co Process for preparing phenyldichloro-acetamidopropanediols
US2744136A (en) * 1953-02-16 1956-05-01 Du Pont Amides of sulfonylserinophenones
US2742500A (en) * 1953-12-22 1956-04-17 Du Pont Resolution of phenylaminopropanediols and intermediates
US2759970A (en) * 1956-05-09 1956-08-21 Sterling Drug Inc Acylamidoaceto-mercaptophenones
US3962271A (en) * 1974-03-04 1976-06-08 Tenneco Chemicals, Inc. Monocyclic polyoxymethyleneoxazolidines and biocidal compositions containing same
US4235892A (en) * 1979-02-05 1980-11-25 Schering Corporation, Patent Dept. 1-Aryl-2-acylamido-3-fluoro-1-propanols, methods for their use as antibacterial agents and compositions useful therefor
US5105009A (en) * 1983-06-02 1992-04-14 Zambon S.P.A. Intermediates for the preparation of 1-(phenyl)-1-hydroxy-2-amino-3-fluoropropane derivatives
DE3486438T2 (de) * 1983-06-02 1998-08-13 Schering Plouth Ltd Verfahren zur Herstellung von 1-(Phenyl)-1-hydroxy-2-amino-3-fluor-propan-Derivaten
IT1164387B (it) * 1983-08-05 1987-04-08 Zambon Spa Derivati n-sostituiti dell'1-(4'-alchilsulfonilfenil)-2-ammino-1,3-propandiolo
IT1164389B (it) * 1983-08-05 1987-04-08 Zambon Spa Derivati n-sostituiti dell'1-(4'-alchiltiofenil)-2-ammino-1,3-propandiolo
US4782163A (en) * 1984-10-05 1988-11-01 Smithkline Beckman Corporation 2-(2-halo-3,4-dimethoxybenzyl)-5-(4-methoxyphenyl)-oxazolidines
US4723986A (en) * 1986-05-19 1988-02-09 Stauffer Chemical Company Herbicidal oxazolidines and methods of use

Also Published As

Publication number Publication date
IT1237798B (it) 1993-06-17
EP0423705A3 (en) 1992-05-06
US5284966A (en) 1994-02-08
JPH03188050A (ja) 1991-08-16
DE69015956T2 (de) 1995-06-08
IT8922075A0 (it) 1989-10-20
GR3015686T3 (en) 1995-07-31
JP2852801B2 (ja) 1999-02-03
ATE116957T1 (de) 1995-01-15
EP0423705B1 (de) 1995-01-11
EP0423705A2 (de) 1991-04-24
US5401852A (en) 1995-03-28
DK0423705T3 (da) 1995-03-27
US5202484A (en) 1993-04-13
ES2066931T3 (es) 1995-03-16

Similar Documents

Publication Publication Date Title
DE69015956T2 (de) Verfahren zur stereochemischen Inversion von (2S,3S)-2-Amino-3-phenyl-1,3-Propandiolen in ihre (2R,3R)-Enantiomere.
DE69738457D1 (de) Verfahren zur Herstellung von Oxazolidinonen
ATE121066T1 (de) Verfahren zur herstellung von 6,12-dihydro-6- hydroxy-cannabidiol und dessen anwendung zur herstellung von trans-delta-9- tetrahydrocannabinol.
ATE234294T1 (de) Verfahren zur herstellung von n-(4-cyan-3- trifluormethylphenyl)-3-(4-flurophenylsulfonyl) 2-hydroxy-2-methylpropionamid
ES2159296T3 (es) Procedimiento para preparar 2,2-difluorocetena silil acetales y esteres de acido alfa,alfa-difluoro-beta-sililoxi-1,3-dioxolano-4-propanoico.
ATE112780T1 (de) Stabile form von cephradin, verfahren zu dessen herstellung und darin verwendete zwischenprodukte.
ATE397088T1 (de) Verfahren zur herstellung von (s)- oder (r)-3,3,3-trifluor-2-hydroxy-2-methylpropionsaü e
DE3764875D1 (de) Verfahren zur herstellung von penemderivaten.
ATE132535T1 (de) Verfahren zur diskontinuierlichen herstellung von l-carnitin auf mikrobiologischem weg
AU1083395A (en) Method for making intermediates useful in synthesis of retroviral protease inhibitors
DE59009951D1 (de) Verfahren zur Herstellung von Zwischenprodukten und zur Synthese von N-(2-Hydroxyethyl)-2-hydroxymethyl-3,4,5-trihydroxypiperidine.
ATE193280T1 (de) Verfahren zur herstellung von beta-amino-alpha- hydroxycarbonsäuren und deren derivaten
DE68916805T2 (de) Verfahren zur herstellung von tocopherolen.
DE69016380T2 (de) Verfahren zur Herstellung von molluskiziden 2,4,5-Tribrompyrrol-3-Carbonitrilen.
DE69324193D1 (de) Verfahren zur Herstellung von Enantiomeren von Dropropizin
DE69407789D1 (de) Verfahren zur herstellung von (s)-4-aminohepta-5,6-diencarbon-säure und intermediate
DE3766898D1 (de) 4-benzyloxy-3-pyrrolin-2-on, dessen herstellung und verwendung zur synthese von tetramsaeure.
ATE61366T1 (de) Industrielles verfahren zur synthese von n-((1'allyl-2'-pyrrolidinyl)methyl>-2-methoxy-4,5- azimidobenzamid.
DE59000657D1 (de) Verfahren zur herstellung von crotonobetainhydrochlorid.
DE68904680D1 (de) Carbamatderivate und verfahren zu ihrer herstellung.
DE69608512T2 (de) Verfahren zur Herstellung von benzylsubstituierten Rhodaninederivaten

Legal Events

Date Code Title Description
8364 No opposition during term of opposition