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
Authority: EP; European Patent Office
Prior art keywords: alkoxy; substituted; optical isomer; salt; formula
Prior art date: 1977-08-09
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.)

1977-08-09

Filing date

1978-07-28

Publication date

1979-02-21

1978-07-28 Application filed by Hoechst AG filed Critical Hoechst AG

1979-02-21 Publication of EP0000745A1 publication Critical patent/EP0000745A1/fr

1981-07-15 Application granted granted Critical

1981-07-15 Publication of EP0000745B1 publication Critical patent/EP0000745B1/fr

Status Expired legal-status Critical Current

Links

150000003839 salts Chemical class 0.000 title claims abstract description 18
JCBPETKZIGVZRE-UHFFFAOYSA-N 2-aminobutan-1-ol Chemical compound CCC(N)CO JCBPETKZIGVZRE-UHFFFAOYSA-N 0.000 title claims abstract description 7
238000000034 method Methods 0.000 title abstract description 8
238000002360 preparation method Methods 0.000 title description 2
ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 title 1
230000003287 optical effect Effects 0.000 claims abstract description 13
150000001875 compounds Chemical class 0.000 claims abstract description 11
238000004519 manufacturing process Methods 0.000 claims abstract description 4
-1 C 1 -C 4 acyloxy Chemical group 0.000 claims description 22
125000000217 alkyl group Chemical class 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
125000003545 alkoxy group Chemical class 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
125000004430 oxygen atom Chemical group O* 0.000 claims description 4
125000005076 adamantyloxycarbonyl group Chemical group C12(CC3CC(CC(C1)C3)C2)OC(=O)* 0.000 claims description 2
125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 2
125000003435 aroyl group Chemical class 0.000 claims description 2
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 2
125000004104 aryloxy group Chemical group 0.000 claims description 2
125000001584 benzyloxycarbonyl group Chemical class C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Chemical class O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 2
125000001557 phthalyl group Chemical class C(=O)(O)C1=C(C(=O)*)C=CC=C1 0.000 claims description 2
125000002221 trityl group Chemical class [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 claims 1
GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 claims 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
150000001413 amino acids Chemical class 0.000 abstract description 7
238000000926 separation method Methods 0.000 abstract description 4
229930186147 Cephalosporin Natural products 0.000 abstract description 2
229930182555 Penicillin Natural products 0.000 abstract description 2
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 abstract description 2
239000003242 anti bacterial agent Substances 0.000 abstract description 2
229940088710 antibiotic agent Drugs 0.000 abstract description 2
229940124587 cephalosporin Drugs 0.000 abstract description 2
150000001780 cephalosporins Chemical class 0.000 abstract description 2
229940049954 penicillin Drugs 0.000 abstract description 2
239000007858 starting material Substances 0.000 abstract description 2
125000002252 acyl group Chemical group 0.000 abstract 1
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 5
150000001412 amines Chemical class 0.000 description 4
KAGSUJOTNBINKR-UHFFFAOYSA-N 2-acetamido-2-(4-methoxyphenyl)acetic acid Chemical compound COC1=CC=C(C(NC(C)=O)C(O)=O)C=C1 KAGSUJOTNBINKR-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
WFRVJRZGHCTEGP-UHFFFAOYSA-N acetyl 2-acetamido-2-(4-hydroxyphenyl)acetate Chemical compound C(C)(=O)NC(C(=O)OC(C)=O)C1=CC=C(C=C1)O WFRVJRZGHCTEGP-UHFFFAOYSA-N 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
239000000725 suspension Substances 0.000 description 2
JVVXZOOGOGPDRZ-SLFFLAALSA-N [(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine Chemical compound NC[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 JVVXZOOGOGPDRZ-SLFFLAALSA-N 0.000 description 1
150000003862 amino acid derivatives Chemical class 0.000 description 1
229960003022 amoxicillin Drugs 0.000 description 1
LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 description 1
229960000723 ampicillin Drugs 0.000 description 1
AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
KMPWYEUPVWOPIM-KODHJQJWSA-N cinchonidine Chemical compound C1=CC=C2C([C@H]([C@H]3[N@]4CC[C@H]([C@H](C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-KODHJQJWSA-N 0.000 description 1
KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229910052736 halogen Chemical group 0.000 description 1
LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

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
US4642205A (en) *	1984-03-01	1987-02-10	Alkaloida Vegyeszeti Gyar	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

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

1977
- 1977-08-09 DE DE19772735834 patent/DE2735834A1/de not_active Withdrawn
1978
- 1978-07-28 EP EP78100531A patent/EP0000745B1/fr not_active Expired
- 1978-07-28 DE DE7878100531T patent/DE2860839D1/de not_active Expired
- 1978-08-04 DD DD78207128A patent/DD137580A5/xx unknown
- 1978-08-04 BG BG040601A patent/BG35593A3/xx unknown
- 1978-08-07 HU HU78HO2093A patent/HU178248B/hu unknown
- 1978-08-07 US US05/931,529 patent/US4182899A/en not_active Expired - Lifetime
- 1978-08-07 CS CS785160A patent/CS203200B2/cs unknown
- 1978-08-07 IT IT26559/78A patent/IT1098014B/it active
- 1978-08-07 IL IL55293A patent/IL55293A/xx unknown
- 1978-08-08 AT AT577278A patent/AT359997B/de not_active IP Right Cessation
- 1978-08-08 IE IE1611/78A patent/IE47236B1/en unknown
- 1978-08-08 SU SU782645702A patent/SU913937A3/ru active
- 1978-08-08 CA CA308,911A patent/CA1110653A/fr not_active Expired
- 1978-08-09 JP JP9628578A patent/JPS5430132A/ja active Pending

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

Legal Events

Date	Code	Title	Description
1979-01-02	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
1979-02-21	AK	Designated contracting states	Designated state(s): BE CH DE FR GB NL SE
1979-10-31	17P	Request for examination filed
1981-05-16	GRAA	(expected) grant	Free format text: ORIGINAL CODE: 0009210
1981-07-15	AK	Designated contracting states	Designated state(s): BE CH DE FR GB NL SE
1981-10-22	REF	Corresponds to:	Ref document number: 2860839 Country of ref document: DE Date of ref document: 19811022
1984-06-18	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
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1987-01-31	BERE	Be: lapsed	Owner name: HOECHST A.G. Effective date: 19860731
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2016-09-14	STAA	Information on the status of an ep patent application or granted ep patent	Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

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