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

Info

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

Links

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
DE2735834 1977-08-09
DE19772735834 DE2735834A1 (de) 1977-08-09 1977-08-09 Trennung von aminosaeuren in optische antipoden

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
HU193199B (en) * 1984-03-01 1987-08-28 Budapesti Mueszaki Egyetem Process for preparing optically active alpha-amino-beta-phenyl-propionic acids
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
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
NL268416A (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
DD137580A5 (de) 1979-09-12
IL55293A (en) 1982-09-30
AT359997B (de) 1980-12-10
EP0000745B1 (fr) 1981-07-15
CA1110653A (fr) 1981-10-13
IE781611L (en) 1979-02-09
DE2860839D1 (en) 1981-10-22
IT7826559A0 (it) 1978-08-07
ATA577278A (de) 1980-05-15
IE47236B1 (en) 1984-01-25
US4182899A (en) 1980-01-08
HU178248B (en) 1982-04-28
IL55293A0 (en) 1978-10-31
IT1098014B (it) 1985-08-31
SU913937A3 (en) 1982-03-15
JPS5430132A (en) 1979-03-06
DE2735834A1 (de) 1979-02-22
CS203200B2 (en) 1981-02-27
BG35593A3 (en) 1984-05-15

Similar Documents

Publication Publication Date Title
DE4345311C1 (de) Verfahren zur Herstellung und/oder Reinigung von Clavulansäure
EP0612322A1 (fr) Procede de separation de l'acide 5-methyl-tetrahydrofollique
AT399155B (de) Neue alkylendiammonium-diclavulanat-derivate, verfahren zu deren herstellung sowie deren verwendung
DE2812041A1 (de) Optisch aktive aminosaeure-mandelsaeure- komplexe, verfahren zu deren herstellung und verfahren zur herstellung optisch aktiver aminosaeuren oder mandelsaeure
EP0312726B1 (fr) Sels optiquement actifs d'un acide thiazolidine-4-carboxylique substitué et de 3-chloro-2-hydroxypropyl triméthylammonium, préparation et utilisation
EP0000745B1 (fr) Sel d'un isomère optiquement actif de phényl-glycine et d'un isomère optiquement actif d'amino-2-butanol et procédé pour sa préparation
EP0625137B1 (fr) Procede de separation des racemates du verapamil
DE69912773T2 (de) Nicht hydratisiertes gabapentin polymorph, herstellungsprozess und verwendung zur herstellung von gabapentin pharmazeutischer reinheit.
DE2926847C2 (fr)
DE2501957C2 (de) Verfahren zur Gewinnung von optisch aktivem p-Hydroxyphenylglycin
DE60104103T2 (de) Verfahren zur herstellung von hochkristallinem natrium cefoperazon
DE2319493C3 (de) Verfahren zur Gewinnung von optisch aktivem a -Phenylglycin-benzolsulfonat durch optische Aufspaltung von DL- a -Phenylglycinbenzolsulfonat
DE2620369C3 (de) Verfahren zur Wiedergewinnung von (l-S)-2-Oxo-bornansulfonat-(10)
DE2240442A1 (de) Verfahren zur herstellung von aminopenicillinen
DE2659048A1 (de) Neue inositphosphatid-derivate und verfahren zur herstellung dieser verbindungen
DE2400489B2 (de) Salze aus D- oder L-N-Methylephedrin und Enamin-Derivaten von a -Aminomonocarbonsäuren, Verfahren zu deren Herstellung und deren Verwendung
CH483398A (de) Verfahren zur Herstellung von Phenylalaninderivaten
DE2512608C2 (de) Verfahren zur Herstellung von D-Penicillamin
DE2612615A1 (de) Verfahren zur herstellung von optisch aktivem alpha-phenylglycin und zwischenprodukt dafuer
EP0728736A1 (fr) Procédé pour la préparation de tert-leucinol optiquement actif et son utilisation
DE2150267C3 (de) Verfahren zur Herstellung von Peptiden
DE2843040A1 (de) Verfahren zur herstellung von n-(4'- chlor-3'-sulfamoyl-benzolsulfonyl)-n-methyl- 2-aminomethyl-2-methyl-tetrahydrofuran
DE859026C (de) Verfahren zur Herstellung von Folinsaeuren
DE4234000A1 (de) Verfahren zur Racemattrennung von Anipamil
EP0195329B1 (fr) Procédé pour la préparation d'antipodes-(-) du cyclohexyl-1-diméthyl-4,4-hydroxy-3-(triazol-1,2,4-yl-1)-2 pentène-1-(E)

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Designated state(s): BE CH DE FR GB NL SE

17P Request for examination filed
GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Designated state(s): BE CH DE FR GB NL SE

REF Corresponds to:

Ref document number: 2860839

Country of ref document: DE

Date of ref document: 19811022

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: CH

Payment date: 19840618

Year of fee payment: 7

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 19840621

Year of fee payment: 7

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: BE

Payment date: 19840630

Year of fee payment: 7

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 19840810

Year of fee payment: 7

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: SE

Payment date: 19840930

Year of fee payment: 7

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: NL

Payment date: 19850731

Year of fee payment: 8

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Effective date: 19860402

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SE

Effective date: 19860729

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: CH

Effective date: 19860731

Ref country code: BE

Effective date: 19860731

BERE Be: lapsed

Owner name: HOECHST A.G.

Effective date: 19860731

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Effective date: 19870201

NLV4 Nl: lapsed or anulled due to non-payment of the annual fee
PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19870331

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

GBPC Gb: european patent ceased through non-payment of renewal fee
REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Effective date: 19881117

EUG Se: european patent has lapsed

Ref document number: 78100531.9

Effective date: 19870505

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT