EP0000745B1 - Salz eines optischen isomeren Phenyl-glycins und eines optischen isomeren 2-Aminobutanols, Verfahren zu deren Herstellung - Google Patents

Salz eines optischen isomeren Phenyl-glycins und eines optischen isomeren 2-Aminobutanols, Verfahren zu deren Herstellung Download PDF

Info

Publication number
EP0000745B1
EP0000745B1 EP78100531A EP78100531A EP0000745B1 EP 0000745 B1 EP0000745 B1 EP 0000745B1 EP 78100531 A EP78100531 A EP 78100531A EP 78100531 A EP78100531 A EP 78100531A EP 0000745 B1 EP0000745 B1 EP 0000745B1
Authority
EP
European Patent Office
Prior art keywords
alkoxy
salt
optionally substituted
optically active
carbonyl
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
Application number
EP78100531A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0000745A1 (de
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/de
Application granted granted Critical
Publication of EP0000745B1 publication Critical patent/EP0000745B1/de
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 i --C 4- alkoxy, aryloxy, C 1 -C 4 -acyloxy, aralkyloxy, the optionally. is substituted with a maximum of 3 halogen atoms or nitro groups and contains a maximum of 4 carbon atoms in the alkyl radical, tert-alkoxy with a tertiary carbon atom bonded to the oxygen atom, aikoxycarbonyloxy or picolyloxycarbonyloxy and Y is aliphatic acyl, the counter.
  • benzylidene may also be substituted with up to 3-halogen atoms or may contain further carbonyl groups, optionally halogen-substituted aroyl, or alkyl, alkoxy, nitro, phthalyl, trityl, optionally alkyl-, alkoxy- or halogen-substituted benzylidene, acetylisopropylidene, benzoylisopropylidene, 5,5-dimethyl-3-oxo-cyclohexen-1-yl, trichloroethyloxycarbonyl, benzyloxycarbonyl, optionally alkyl, alkoxy or halogen-substituted or substituted with a nitro group or ⁇ B (OH) 2 , tert-alkoxy with a tertiary carbon atom, which is attached to the oxygen atom, means adamantyloxycarbonyl, diphenylisopropyloxy
  • optically active compounds of the formula mentioned are used as starting material for the production of semi-synthetic antibiotics of the cephalosporin or penicellin 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 (cf. FR-A 2107926)
  • 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.
  • AT-PS 334 345 salts from optical isomers of N-acyl derivatives of dimethoxyphenylalanine and 2-aminobutanol are described. The yields are also low.
  • the amino group of the amino acid or one of its derivatives is substituted in order to increase the acidity of the amino acid.
  • These derivatives of the amino acids form the corresponding salts with 2-aminobutanol more easily than the amino acids themselves.
  • the salts are generally prepared in water or a lower alkanol, preferably methanol, ethanol or isopropanol, one of the two salts precipitating from a racemic base Compound of formula I and optically active 2-aminobutanol can be formed.
  • the method according to the invention is superior to known methods in that the op . table 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 Salz eines optischen isomeren Phenyl-glycins und eines optischen isomeren 2-Aminobutanols, Verfahren zu deren Herstellung Expired EP0000745B1 (de)

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 EP0000745A1 (de) 1979-02-21
EP0000745B1 true EP0000745B1 (de) 1981-07-15

Family

ID=6015982

Family Applications (1)

Application Number Title Priority Date Filing Date
EP78100531A Expired EP0000745B1 (de) 1977-08-09 1978-07-28 Salz eines optischen isomeren Phenyl-glycins und eines optischen isomeren 2-Aminobutanols, Verfahren zu deren Herstellung

Country Status (14)

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

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1985003932A1 (en) * 1984-03-01 1985-09-12 Alkaloida Vegyészeti Gyár Novel diastereomer salts of phenylalanine and n-acyl derivatives thereof and process for the separation of optically active phenylalanine and n-acyl derivatives thereof
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
IT1226903B (it) * 1988-07-12 1991-02-21 Mini Ricerca Scient Tecnolog Processo per la sintesi di aminoacidi otticamente attivi
FR2672593B1 (fr) * 1991-02-08 1994-05-20 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
CN102887836B (zh) * 2011-07-18 2014-03-26 西南大学 L-苯甘氨酸衍生物及其应用

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL129419C (cs) * 1960-08-19
US3869505A (en) * 1970-09-24 1975-03-04 Beecham Group Ltd DL-2-(4-hydroxyphenyl)-glycine-N,O-diacetate and salts
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
YU36484B (en) * 1973-06-07 1984-02-29 Pliva Pharm & Chem Works Process for preparing l-(-)-2-methyl-3-(3,4-dihydroxyphenyl)-alanine
JPS5069039A (cs) * 1973-10-23 1975-06-09
JPS50116434A (cs) * 1974-03-01 1975-09-11
JPS5152154A (en) * 1974-10-26 1976-05-08 Sankyo Co nn karubometokishifuenirugurishinno kogakubunkatsuho

Also Published As

Publication number Publication date
DE2735834A1 (de) 1979-02-22
DE2860839D1 (en) 1981-10-22
IE47236B1 (en) 1984-01-25
EP0000745A1 (de) 1979-02-21
US4182899A (en) 1980-01-08
HU178248B (en) 1982-04-28
IT1098014B (it) 1985-08-31
JPS5430132A (en) 1979-03-06
IT7826559A0 (it) 1978-08-07
IL55293A0 (en) 1978-10-31
ATA577278A (de) 1980-05-15
CS203200B2 (en) 1981-02-27
AT359997B (de) 1980-12-10
IE781611L (en) 1979-02-09
DD137580A5 (de) 1979-09-12
IL55293A (en) 1982-09-30
BG35593A3 (en) 1984-05-15
SU913937A3 (en) 1982-03-15
CA1110653A (en) 1981-10-13

Similar Documents

Publication Publication Date Title
WO1993010118A1 (de) Verfahren zur trennung von 5-methyl-tetrahydrofolsäure
EP0000745B1 (de) Salz eines optischen isomeren Phenyl-glycins und eines optischen isomeren 2-Aminobutanols, Verfahren zu deren Herstellung
EP0625137B1 (de) Verfahren zur racemattrennung von verapamil
EP0312726B1 (de) Optisch aktive Salze aus einem substituierten Thiazolidin-4-carboxylat und 3-Chlor-2-hydroxypropyltrimethylammonium, deren Herstellung und Verwendung
EP0237902A2 (de) Verfahren zur Herstellung des (-)-Antipoden des (E)-1-Cyclohexyl-4,4-dimethyl-3-hydroxy-2-(1,2,4-triazol-1-yl)-pent-1-ens
DE2501957C2 (de) Verfahren zur Gewinnung von optisch aktivem p-Hydroxyphenylglycin
EP0126934B1 (de) Verfahren zur Herstellung von 1,1-disubstituierten Thioharnstoffen
DE2400489B2 (de) Salze aus D- oder L-N-Methylephedrin und Enamin-Derivaten von a -Aminomonocarbonsäuren, Verfahren zu deren Herstellung und deren Verwendung
DE1518337A1 (de) Neue Roentgenkontrastmittel und Verfahren zur Herstellung derselben
DE2141765A1 (de) 4-chlor-4-thiazolin-2-one und verfahren zu deren herstellung
DE69113365T2 (de) Optisch aktives Morpholinooxobutansäure-Hydroxybinaphthalinderivat und seine Herstellung.
DE2150267C3 (de) Verfahren zur Herstellung von Peptiden
DE568944C (de) Verfahren zur Darstellung von Bis- (halogen-oxyaryl)-sulfiden
DE1933187B2 (de) Verfahren zur Herstellung von 7-Aminocephalosporansäure
EP0073052B1 (de) Verfahren zur Trennung des Racemats S-(Carboxymethyl)-(RS)-cystein (A)
AT371448B (de) Verfahren zur herstellung von neuen cis-4a-phenyl -isochinolin-derivaten und ihren saeureadditionssalzen
EP0478721B1 (de) Neue benzocycloalkencarbonsäure und verfahren zu ihrer herstellung
DE869964C (de) Verfahren zur Herstellung von Cholinderivaten
DE1192209B (de) Verfahren zur Herstellung von Estern von quaternaeren Ammoniumverbindungen
DE1445692A1 (de) Verfahren zur Herstellung von Piperazinderivaten
DE1057133B (de) Verfahren zur Herstellung neuer, pharmakologisch wirkender 1, 1-Diphenyl-2-aminoalkanole
EP0315097A2 (de) Neue Acyllabdan-Derivate, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
DE2535693A1 (de) Neue ester von pgf tief 2alpha , 15(s)-15-methyl-pgf tief 2alpha und 15(r)-15-methyl-pgf tief 2alpha
DE2060217A1 (de) Verfahren zur Herstellung von Dialkylhalogenalkylphosphinoxyden
DE2154437A1 (de) Verfahren zur Herstellung von substituierten alpha-Naphthoxyacetamiden

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