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EP0000745A1 - Sel d'un isomère optiquement actif de phényl-glycine et d'un isomère optiquement actif d'amino-2-butanol et procédé pour sa préparation - Google Patents

Sel d'un isomère optiquement actif de phényl-glycine et d'un isomère optiquement actif d'amino-2-butanol et procédé pour sa préparation Download PDF

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Publication number
EP0000745A1
EP0000745A1 EP7878100531A EP78100531A EP0000745A1 EP 0000745 A1 EP0000745 A1 EP 0000745A1 EP 7878100531 A EP7878100531 A EP 7878100531A EP 78100531 A EP78100531 A EP 78100531A EP 0000745 A1 EP0000745 A1 EP 0000745A1
Authority
EP
European Patent Office
Prior art keywords
alkoxy
substituted
optical isomer
salt
formula
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.)
Granted
Application number
EP7878100531A
Other languages
German (de)
English (en)
Other versions
EP0000745B1 (fr
Inventor
Yung Bog Dr. Chae
Dae Whang Kim
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.)
Hoechst AG
Original Assignee
Hoechst AG
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 Hoechst AG filed Critical Hoechst AG
Publication of EP0000745A1 publication Critical patent/EP0000745A1/fr
Application granted granted Critical
Publication of EP0000745B1 publication Critical patent/EP0000745B1/fr
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B57/00—Separation of optically-active compounds

Definitions

  • the present invention relates to the separation into optical antipodes of compounds of the formula I. wherein XH, OH, C 1 -C 4 alkoxy, aryloxy, C 1 -C 4 acyloxy, aralkyloxy, which is optionally.substituted with at most 3 halogen atoms or nitro groups and contains at most 4 carbon atoms in the alkyl radical, tert.-alkoxy with one tertiary carbon atom bonded to the oxygen atom, alkoxycarbonyloxy or picolyloxycarbonyloxy and Y is aliphatic acyl, which may optionally be substituted with up to 3-halogen atoms or which may contain further carbonyl groups, optionally halogen-substituted aroyl, or alkyl, alkoxy, nitro, phthalyl, trityl , optionally alkyl, alkoxy or halogen substituted Benzylidene, acetylisoprop
  • optically active compounds of the formula mentioned are used as starting material for the production of semisynthetic antibiotics of the cephalosporin or penicillin type, for example ampicillin or amoxycillin.
  • the invention relates to a new process for the preparation of the optically active compounds of the above formula using optically active 2-aminobutanol.
  • optically active natural amines such as cinchonidine or dehydroabiethylamine
  • these natural amines are very expensive and the separation yields are low.
  • recovery of these natural amines for further use is limited because some of these amines are destroyed during the separation process, which is carried out at high temperatures.
  • amino group of the amino acid or one of its derivatives is substituted for acidity
  • the salts are generally prepared in water or a lower alkanol, preferably methanol, ethanol or isopropanol, one of the two salts precipitating out, starting from a racemi see compound of formula I and optically active 2-aminobutanol can be formed.
  • the process according to the invention is superior to known processes in that the optical purity is higher than 99% and higher yields are obtained.
  • amino acid derivatives are converted into the amino acids or into an amino acid which is either still substituted on the amino group or on the phenyl ring.
  • the invention is illustrated by the following examples.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP78100531A 1977-08-09 1978-07-28 Sel d'un isomère optiquement actif de phényl-glycine et d'un isomère optiquement actif d'amino-2-butanol et procédé pour sa préparation Expired EP0000745B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19772735834 DE2735834A1 (de) 1977-08-09 1977-08-09 Trennung von aminosaeuren in optische antipoden
DE2735834 1977-08-09

Publications (2)

Publication Number Publication Date
EP0000745A1 true EP0000745A1 (fr) 1979-02-21
EP0000745B1 EP0000745B1 (fr) 1981-07-15

Family

ID=6015982

Family Applications (1)

Application Number Title Priority Date Filing Date
EP78100531A Expired EP0000745B1 (fr) 1977-08-09 1978-07-28 Sel d'un isomère optiquement actif de phényl-glycine et d'un isomère optiquement actif d'amino-2-butanol et procédé pour sa préparation

Country Status (14)

Country Link
US (1) US4182899A (fr)
EP (1) EP0000745B1 (fr)
JP (1) JPS5430132A (fr)
AT (1) AT359997B (fr)
BG (1) BG35593A3 (fr)
CA (1) CA1110653A (fr)
CS (1) CS203200B2 (fr)
DD (1) DD137580A5 (fr)
DE (2) DE2735834A1 (fr)
HU (1) HU178248B (fr)
IE (1) IE47236B1 (fr)
IL (1) IL55293A (fr)
IT (1) IT1098014B (fr)
SU (1) SU913937A3 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5041637A (en) * 1988-07-12 1991-08-20 Presidenza Del Consiglio Del Ministri-Ufficio Del Ministro Per Il Coordinamento Delle Iniziatjvo Per La Ricerca Scientifica E. Technologica Process for the synthesis of optically active aminoacids
FR2672593A1 (fr) * 1991-02-08 1992-08-14 Beecham Sa Laboratoires Nouveaux composes utiles pour la resolution de la dl-n-acetyle ou la dl-n-haloacetyl-hydroxyphenylglycine.
US5583259A (en) * 1991-02-08 1996-12-10 Les Laboratoires Beecham S.A. 2-(RO)-1-(R) ethylamines
CN102887836A (zh) * 2011-07-18 2013-01-23 西南大学 L-苯甘氨酸衍生物及其应用

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1985003932A1 (fr) * 1984-03-01 1985-09-12 Alkaloida Vegyészeti Gyár Nouveaux sels diastereomeres de phenylalanine et ses derives n-acyliques et procede de separation de phenylalanine optiquement actives et de ses derives n-acyliques
HU193199B (en) * 1984-03-01 1987-08-28 Budapesti Mueszaki Egyetem Process for preparing optically active alpha-amino-beta-phenyl-propionic acids
JPH01155119A (ja) * 1987-12-14 1989-06-19 Rinnai Corp 燃焼制御装置

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2107926A1 (fr) * 1970-09-24 1972-05-12 Beecham Group Ltd
AT334345B (de) * 1973-06-07 1976-01-10 Pliva Pharm & Chem Works Verfahren zur herstellung von l- (-) -alpha- methyl -beta- (3,4-dihydroxyphenyl) -alanin

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL129419C (fr) * 1960-08-19
US3904681A (en) * 1971-03-30 1975-09-09 Ciba Geigy Corp Propionic acid
US3796748A (en) * 1972-08-16 1974-03-12 Bristol Myers Co Dehydroabietylammonium d-(-)-2-chloroacetylamino-2-(p-hydroxyphenyl)-acetate
JPS5069039A (fr) * 1973-10-23 1975-06-09
JPS50116434A (fr) * 1974-03-01 1975-09-11
JPS5152154A (en) * 1974-10-26 1976-05-08 Sankyo Co nn karubometokishifuenirugurishinno kogakubunkatsuho

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2107926A1 (fr) * 1970-09-24 1972-05-12 Beecham Group Ltd
AT334345B (de) * 1973-06-07 1976-01-10 Pliva Pharm & Chem Works Verfahren zur herstellung von l- (-) -alpha- methyl -beta- (3,4-dihydroxyphenyl) -alanin

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5041637A (en) * 1988-07-12 1991-08-20 Presidenza Del Consiglio Del Ministri-Ufficio Del Ministro Per Il Coordinamento Delle Iniziatjvo Per La Ricerca Scientifica E. Technologica Process for the synthesis of optically active aminoacids
FR2672593A1 (fr) * 1991-02-08 1992-08-14 Beecham Sa Laboratoires Nouveaux composes utiles pour la resolution de la dl-n-acetyle ou la dl-n-haloacetyl-hydroxyphenylglycine.
WO1992013823A1 (fr) * 1991-02-08 1992-08-20 Les Laboratoires Beecham S.A. Aminoalcools utiles comme agents optiques resolvants
US5583259A (en) * 1991-02-08 1996-12-10 Les Laboratoires Beecham S.A. 2-(RO)-1-(R) ethylamines
CN102887836A (zh) * 2011-07-18 2013-01-23 西南大学 L-苯甘氨酸衍生物及其应用
CN102887836B (zh) * 2011-07-18 2014-03-26 西南大学 L-苯甘氨酸衍生物及其应用

Also Published As

Publication number Publication date
IE47236B1 (en) 1984-01-25
CS203200B2 (en) 1981-02-27
JPS5430132A (en) 1979-03-06
IL55293A0 (en) 1978-10-31
IE781611L (en) 1979-02-09
IL55293A (en) 1982-09-30
US4182899A (en) 1980-01-08
EP0000745B1 (fr) 1981-07-15
DE2735834A1 (de) 1979-02-22
ATA577278A (de) 1980-05-15
IT7826559A0 (it) 1978-08-07
AT359997B (de) 1980-12-10
CA1110653A (fr) 1981-10-13
DE2860839D1 (en) 1981-10-22
SU913937A3 (en) 1982-03-15
HU178248B (en) 1982-04-28
IT1098014B (it) 1985-08-31
DD137580A5 (de) 1979-09-12
BG35593A3 (en) 1984-05-15

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