SU784759A3 - Method of preparing 2-arylpropionic acid enanthiomer - Google Patents

Method of preparing 2-arylpropionic acid enanthiomer Download PDF

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Publication number
SU784759A3
SU784759A3 SU782588501A SU2588501A SU784759A3 SU 784759 A3 SU784759 A3 SU 784759A3 SU 782588501 A SU782588501 A SU 782588501A SU 2588501 A SU2588501 A SU 2588501A SU 784759 A3 SU784759 A3 SU 784759A3
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SU
USSR - Soviet Union
Prior art keywords
text
salt
diluent
enantiomer
proportion
Prior art date
Application number
SU782588501A
Other languages
Russian (ru)
Inventor
Стюарт Никольсон Джон
Гордон Тантум Джеймс
Original Assignee
Дзе Бутс Компани Лимитед (Фирма)
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.)
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Priority claimed from GB9697/77A external-priority patent/GB1596032A/en
Application filed by Дзе Бутс Компани Лимитед (Фирма) filed Critical Дзе Бутс Компани Лимитед (Фирма)
Application granted granted Critical
Publication of SU784759A3 publication Critical patent/SU784759A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
    • C07C59/56—Unsaturated compounds containing hydroxy or O-metal groups containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
    • C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
    • C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Disclosed is a process for increasing the proportion of a desired enantiomer of a 2-arylpropionic acid which comprises heating at a temperature of at least 80.degree.C a mixture comprising an inert liquid organic diluent and a salt of the 2-arylpropionic acid with an enantiomer of a chiral organic nitrogenous base, the base and the diluent being such that the salt of the racemic acid has a solubility of 0.1 to 10% w/v in the diluent at the operating temperature and in whidh process a proportion of the salt is undissolved in the diluent, whereby a proportion of one optical isomer of the acid component of the salt is converted into its enantiomer, and collecting the salt of which the acid component has an increased proportion of that enantiomer.

Description

одного, или более, Органического соединени . По окончании нагревани  гор чие смеси фильтруют через обогреваемую паром воронку Бюхнера, соли промывают гор чим разбавителем, высушивают в вакууме, подкисл ют разбавленной серной или сол ной кислотой и кислые смеси экстрагируют эфиром.one or more organic compounds. At the end of the heating, the hot mixtures are filtered through a Buchner funnel, the salts are washed with a hot diluent, dried under vacuum, acidified with dilute sulfuric or hydrochloric acid, and the acid mixtures are extracted with ether.

Эфирные экстракты промывают водой, высушивают и выпаривают с образованием 2-арилпропионовых кислот, имеющих различную оптическую активность, из кислотного компонента соли в начале опыта.The ether extracts are washed with water, dried and evaporated to form 2-aryl-propionic acids, which have different optical activity, from the acid component of the salt at the beginning of the experiment.

Подробности и результаты различных примеров приведены в табл. 1.,Details and results of various examples are given in table. one.,

Продолжение табл.Continued table.

Claims (1)

<claim-text><table border="1"> <tbody><tr><td> 11 -</td><td> ( + )</td><td> -сС- (2-метоксифенил) -этил-</td></tr> <tr><td colspan="3"> амин.</td></tr> <tr><td> 12</td><td> (-)</td><td> (2-метоксифенил) -этил-</td></tr> <tr><td colspan="3"> амин.</td></tr> <tr><td> м -</td><td> (-)</td><td> -сб- (4-фторфенил)-этиламин.</td></tr> <tr><td> N ' -</td><td> (4)</td><td> "об" (2-фторфенил) -этиламин.</td></tr> <tr><td> 0 -</td><td> (-)</td><td> -«£- (2-хлорфенил)-этиламин.</td></tr> <tr><td> Р -</td><td> (-)</td><td> -оСг (3-фторфенил) -этиламин. Растворители</td></tr> </tbody></table> <claim-text>К - Нефтяная фракция, интервал т. кип. 112-130°С, (-) -оС-пинен.</claim-text> <claim-text>Т - мирцен.</claim-text> <claim-text>81 - 85% К +15% толуол, и2 - 67%« + 33% толуол.</claim-text> <claim-text>V - Нефтяная фракция, интервал</claim-text> <claim-text>т.кип. 120-160 С.</claim-text> <claim-text>У - Нефтяная фракция, интервал</claim-text> <claim-text>т.кип. 125-160°С.</claim-text> <claim-text>X - Октан.</claim-text><claim-text> <table border = "1"> <tbody> <tr> <td> 11 - </ td> <td> (+) </ td> <td> -cC- (2-methoxyphenyl) -ethyl - </ td> </ tr> <tr> <td colspan = "3"> Amin. </ td> </ tr> <tr> <td> 12 </ td> <td> (-) </ td> <td> (2-methoxyphenyl) -ethyl - </ td> </ tr> <tr> <td colspan = "3"> Amin. </ td> </ tr> <tr> <td> m - </ td> <td> (-) </ td> <td> -sb- (4-fluorophenyl) -ethylamine. </ td> </ tr> <tr> <td> N '- </ td> <td> (4) </ td> <td> "about" (2-fluorophenyl) -ethylamine. </ td> </ tr> <tr> <td> 0 - </ td> <td> (-) </ td> <td> - “£ - (2-chlorophenyl) -ethylamine. </ Td> </ tr> <tr> <td> P - </ td> <td> (-) </ td> <td> -oCg (3-fluorophenyl) -ethylamine. Solvents </ td> </ tr> </ tbody> </ table> <claim-text> K - Oil fraction, interval t. Kip. 112-130 ° C, (-) -oC-pinene. </ Claim-text> <claim-text> T - myrcene. </ claim-text> <claim-text> 81 - 85% K + 15% toluene, and 2 - 67% "+ 33% toluene. </ claim-text> <claim-text> V - Oil fraction, interval </ claim-text> <claim-text> ft. 120-160 C. </ claim-text> <claim-text> Y - Oil fraction, interval </ claim-text> <claim-text> ft. 125-160 ° C. </ Claim-text> <claim-text> X - Octane. </ claim-text>
SU782588501A 1977-03-08 1978-03-07 Method of preparing 2-arylpropionic acid enanthiomer SU784759A3 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9697/77A GB1596032A (en) 1977-03-08 1977-03-08 Resolution of optically active 2-arylpropionic acids
GB194678 1978-01-18

Publications (1)

Publication Number Publication Date
SU784759A3 true SU784759A3 (en) 1980-11-30

Family

ID=26237091

Family Applications (1)

Application Number Title Priority Date Filing Date
SU782588501A SU784759A3 (en) 1977-03-08 1978-03-07 Method of preparing 2-arylpropionic acid enanthiomer

Country Status (29)

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JP (1) JPS53112841A (en)
AT (1) AT360508B (en)
AU (1) AU521708B2 (en)
BG (1) BG28567A3 (en)
CA (1) CA1105942A (en)
CH (1) CH638482A5 (en)
CS (1) CS222255B2 (en)
DD (1) DD136261A5 (en)
DE (1) DE2809794A1 (en)
DK (1) DK154418C (en)
EG (1) EG13345A (en)
ES (1) ES467606A1 (en)
FI (1) FI66828C (en)
FR (1) FR2383155A1 (en)
GR (1) GR64816B (en)
HU (1) HU178810B (en)
IE (1) IE46476B1 (en)
IN (1) IN147834B (en)
IT (1) IT1202818B (en)
LU (1) LU79186A1 (en)
NL (1) NL189126C (en)
NO (1) NO146197C (en)
NZ (1) NZ186644A (en)
PH (1) PH13333A (en)
PL (1) PL110888B1 (en)
PT (1) PT67743A (en)
SE (1) SE436422B (en)
SU (1) SU784759A3 (en)
YU (1) YU41472B (en)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2826952A1 (en) * 1978-06-20 1980-01-10 Bayer Ag ENANTIOMER SEPARATION OF CHIRAL CARBONIC ACIDS
PH15674A (en) * 1979-07-06 1983-03-11 Syntex Corp Process for the resolution of d,1 2-(6-methoxy-2-naphthyl)propionic acid
JPS57145830A (en) * 1981-03-06 1982-09-09 Hiroyuki Nohira Optical resolution of 2-(4-chlorophenyl)-3-methylbutanoic acid
JPH01126425U (en) * 1988-02-23 1989-08-29
DE3824353A1 (en) * 1988-07-19 1990-01-25 Paz Arzneimittelentwicklung METHOD FOR SEPARATING MIXED ENANTIOMER ARYLPROPIONIC ACIDS
DE4028906A1 (en) * 1990-09-12 1992-03-19 Paz Arzneimittelentwicklung MEDICINAL PRODUCTS AND THEIR PREPARATION AND THEIR USE IN THE CONTROL OF PAIN AND / OR DEFENSE AND / OR FEVER OF ANIMALS AND PEOPLE
DE4319438C1 (en) * 1993-06-11 1994-06-01 Gerd Dr Dr Geislinger Analgesic and/or antiinflammatory medicaments - contg. sepd enantiomers of ketoprofen
JP3782834B2 (en) 1994-10-26 2006-06-07 株式会社トクホン Analgesic anti-inflammatory patch
DE19717429A1 (en) * 1997-04-25 1998-12-24 Bayer Ag Production of enantiomerically pure biaryl ketocarboxylic acids
JP2012516874A (en) 2009-02-06 2012-07-26 ディーエスエム アイピー アセッツ ビー．ブイ． Method for synthesizing chiral α-arylpropionic acid derivatives

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL23268A (en) * 1964-05-07 1969-02-27 Merck & Co Inc Anti-inflammatory compositions containing 4-phenyl-alpha-methyl-phenylacetic acid
FR2015728A1 (en) * 1968-04-18 1970-04-30 Lilly Co Eli Anti-inflammatory substd-phenylalkanoic acids and - derivs
US3686183A (en) * 1969-03-24 1972-08-22 Syntex Corp Preparation of optical isomers of arylalkylacetic acids

Also Published As

Publication number Publication date
LU79186A1 (en) 1978-09-18
PT67743A (en) 1978-04-01
HU178810B (en) 1982-06-28
FR2383155A1 (en) 1978-10-06
PL110888B1 (en) 1980-08-30
JPS626536B2 (en) 1987-02-12
NL7802520A (en) 1978-09-12
NO146197B (en) 1982-05-10
YU54078A (en) 1984-04-30
EG13345A (en) 1981-06-30
PH13333A (en) 1980-03-13
ATA163478A (en) 1980-06-15
DK154418B (en) 1988-11-14
IE780467L (en) 1978-09-08
NL189126C (en) 1993-01-18
BG28567A3 (en) 1980-05-15
FI66828B (en) 1984-08-31
DK154418C (en) 1989-06-19
FI66828C (en) 1984-12-10
AU3397778A (en) 1979-09-13
FR2383155B1 (en) 1983-12-30
FI780738A (en) 1978-09-09
DE2809794A1 (en) 1978-09-21
PL205161A1 (en) 1979-03-26
DD136261A5 (en) 1979-06-27
CH638482A5 (en) 1983-09-30
CS222255B2 (en) 1983-06-24
SE7802603L (en) 1978-09-09
NO780785L (en) 1978-09-11
AU521708B2 (en) 1982-04-29
GR64816B (en) 1980-06-03
NO146197C (en) 1982-08-18
IE46476B1 (en) 1983-06-29
IN147834B (en) 1980-07-19
IT1202818B (en) 1989-02-09
NL189126B (en) 1992-08-17
CA1105942A (en) 1981-07-28
YU41472B (en) 1987-08-31
DE2809794C2 (en) 1989-08-03
SE436422B (en) 1984-12-10
IT7848320A0 (en) 1978-03-07
AT360508B (en) 1981-01-12
JPS53112841A (en) 1978-10-02
NZ186644A (en) 1980-10-24
ES467606A1 (en) 1978-10-16
DK100878A (en) 1978-09-09

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