CA1127180A - Procede de dedoublement de l'acide dl cis et dl trans chrysanthemique - Google Patents
Procede de dedoublement de l'acide dl cis et dl trans chrysanthemiqueInfo
- Publication number
- CA1127180A CA1127180A CA341,406A CA341406A CA1127180A CA 1127180 A CA1127180 A CA 1127180A CA 341406 A CA341406 A CA 341406A CA 1127180 A CA1127180 A CA 1127180A
- Authority
- CA
- Canada
- Prior art keywords
- acid
- chrysanthemic
- cis
- trans
- salt
- 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
Links
- 238000000034 method Methods 0.000 title claims abstract description 34
- XLOPRKKSAJMMEW-SFYZADRCSA-N (+)-trans-chrysanthemic acid Chemical compound CC(C)=C[C@@H]1[C@@H](C(O)=O)C1(C)C XLOPRKKSAJMMEW-SFYZADRCSA-N 0.000 title claims description 14
- 239000002253 acid Substances 0.000 claims abstract description 55
- 150000003839 salts Chemical class 0.000 claims abstract description 24
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 claims abstract description 12
- 239000003960 organic solvent Substances 0.000 claims abstract description 7
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229960002179 ephedrine Drugs 0.000 claims abstract description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 36
- FMCGSUUBYTWNDP-ONGXEEELSA-N (1R,2S)-2-(dimethylamino)-1-phenyl-1-propanol Chemical compound CN(C)[C@@H](C)[C@H](O)C1=CC=CC=C1 FMCGSUUBYTWNDP-ONGXEEELSA-N 0.000 claims description 18
- FMCGSUUBYTWNDP-UHFFFAOYSA-N N-Methylephedrine Natural products CN(C)C(C)C(O)C1=CC=CC=C1 FMCGSUUBYTWNDP-UHFFFAOYSA-N 0.000 claims description 16
- FMCGSUUBYTWNDP-MWLCHTKSSA-N (1s,2r)-2-(dimethylamino)-1-phenylpropan-1-ol Chemical compound CN(C)[C@H](C)[C@@H](O)C1=CC=CC=C1 FMCGSUUBYTWNDP-MWLCHTKSSA-N 0.000 claims description 15
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 14
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 14
- 229940073569 n-methylephedrine Drugs 0.000 claims description 14
- 241000723353 Chrysanthemum Species 0.000 claims description 12
- 235000007516 Chrysanthemum Nutrition 0.000 claims description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- XLOPRKKSAJMMEW-UHFFFAOYSA-N chrysanthemic acid Chemical compound CC(C)=CC1C(C(O)=O)C1(C)C XLOPRKKSAJMMEW-UHFFFAOYSA-N 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 238000002425 crystallisation Methods 0.000 claims description 4
- 230000008025 crystallization Effects 0.000 claims description 4
- -1 acetate ethyl Chemical compound 0.000 claims 1
- 235000021178 picnic Nutrition 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 4
- 239000002904 solvent Substances 0.000 abstract description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 4
- 238000010908 decantation Methods 0.000 description 4
- 229960002221 methylephedrine Drugs 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLOPRKKSAJMMEW-HTQZYQBOSA-N (-)-cis-chrysanthemic acid Chemical compound CC(C)=C[C@@H]1[C@H](C(O)=O)C1(C)C XLOPRKKSAJMMEW-HTQZYQBOSA-N 0.000 description 2
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XLOPRKKSAJMMEW-JGVFFNPUSA-N (-)-trans-chrysanthemic acid Chemical compound CC(C)=C[C@H]1[C@H](C(O)=O)C1(C)C XLOPRKKSAJMMEW-JGVFFNPUSA-N 0.000 description 1
- VGKZBAMIYUHSMU-UHFFFAOYSA-N 4-[[2-chloroethyl(nitroso)carbamoyl]amino]cyclohexane-1-carboxylic acid Chemical compound OC(=O)C1CCC(NC(=O)N(CCCl)N=O)CC1 VGKZBAMIYUHSMU-UHFFFAOYSA-N 0.000 description 1
- 235000001258 Cinchona calisaya Nutrition 0.000 description 1
- 206010012289 Dementia Diseases 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR78-34591 | 1978-12-08 | ||
| FR7834591A FR2443452A1 (fr) | 1978-12-08 | 1978-12-08 | Nouveau procede de dedoublement de l'acide dl cis et dl trans chrysanthemique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1127180A true CA1127180A (fr) | 1982-07-06 |
Family
ID=9215840
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA341,406A Expired CA1127180A (fr) | 1978-12-08 | 1979-12-06 | Procede de dedoublement de l'acide dl cis et dl trans chrysanthemique |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4257976A (forum.php) |
| JP (1) | JPS56108736A (forum.php) |
| BE (1) | BE880490A (forum.php) |
| CA (1) | CA1127180A (forum.php) |
| CH (1) | CH641751A5 (forum.php) |
| DE (1) | DE2949384A1 (forum.php) |
| ES (1) | ES486670A1 (forum.php) |
| FR (1) | FR2443452A1 (forum.php) |
| HU (1) | HU181948B (forum.php) |
| IT (1) | IT1164774B (forum.php) |
| NL (1) | NL7908881A (forum.php) |
| SE (1) | SE430984B (forum.php) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU543276B2 (en) * | 1981-06-18 | 1985-04-18 | Stauffer Chemical Company | Resolution of dl-trans-chrysanthemic acid |
| US4542235A (en) * | 1982-04-12 | 1985-09-17 | Sumitomo Chemical Company, Limited | Method for producing an optically active 2,2-dimethylcyclopropanecarboxylic acid |
| US4663474A (en) * | 1983-02-22 | 1987-05-05 | Pfizer Inc. | Synthetic intermediates for a chiral 3-(substituted-phenyl)-4-(3-hydroxypropyl) cyclohexanol |
| DE69324362T2 (de) | 1992-06-05 | 1999-08-26 | The Scripps Research Institute | D-enzymzusammensetzungen und verfahren zu deren verwendung |
| US5447897A (en) * | 1993-05-17 | 1995-09-05 | Shell Oil Company | Ethylene oxide catalyst and process |
| ITMI20050231A1 (it) * | 2005-02-17 | 2006-08-18 | Endura Spa | Processo per l'ottenimento di enantiomeri dell'acido crisantemico |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR92748E (fr) * | 1966-01-26 | 1968-12-20 | Roussel Uclaf | Nouveaux composés optiquement actifs et procédé pour leur utilisation au dédoublement de produits racémiques. |
| FR1536458A (fr) * | 1967-07-07 | 1968-08-16 | Roussel Uclaf | Procédé d'obtention de l'acide d-trans chrysanthémique |
| FR1522654A (fr) * | 1966-04-27 | 1968-04-26 | Sumitomo Chemical Co | Procédé de préparation de sel de quinine d'acide (+)-trans-chrysanthème-monocarboxylique de très grande pureté optique |
| FR1507192A (fr) * | 1966-08-26 | 1967-12-29 | Roussel Uclaf | Nouvelles aryl allylsulfones et procédé de préparation |
| US3739019A (en) * | 1969-07-02 | 1973-06-12 | Sumitomo Chemical Co | Preparation of optically active trans chrysanthemic acid |
| BE755498A (fr) * | 1969-09-12 | 1971-02-01 | Sumitomo Chemical Co | Preparation d'acide chrysanthemique optiquement |
| HU165117B (forum.php) * | 1971-08-12 | 1974-06-28 | ||
| BE790240A (fr) * | 1971-10-19 | 1973-02-15 | Sumitomo Chemical Co | Procede de preparation de l'acide mixte (+)-cis, (+)-trans- chrysanthemique |
| JPS5123497B2 (forum.php) * | 1972-01-07 | 1976-07-17 | ||
| JPS4992049A (forum.php) * | 1973-01-09 | 1974-09-03 | ||
| JPS51143647A (en) * | 1975-06-06 | 1976-12-10 | Sumitomo Chem Co Ltd | Process for obtaining optically active trans-2,2-dimethyl-3-(2,2-dichl orovinyl) cyclopropanecarboxylic acid |
-
1978
- 1978-12-08 FR FR7834591A patent/FR2443452A1/fr active Granted
-
1979
- 1979-10-23 SE SE7908765A patent/SE430984B/sv not_active IP Right Cessation
- 1979-11-20 US US06/096,028 patent/US4257976A/en not_active Expired - Lifetime
- 1979-12-06 CA CA341,406A patent/CA1127180A/fr not_active Expired
- 1979-12-06 HU HU79RO1050A patent/HU181948B/hu not_active IP Right Cessation
- 1979-12-07 JP JP15822679A patent/JPS56108736A/ja active Granted
- 1979-12-07 CH CH1087779A patent/CH641751A5/fr not_active IP Right Cessation
- 1979-12-07 DE DE19792949384 patent/DE2949384A1/de active Granted
- 1979-12-07 IT IT51027/79A patent/IT1164774B/it active
- 1979-12-07 BE BE0/198472A patent/BE880490A/fr not_active IP Right Cessation
- 1979-12-07 ES ES486670A patent/ES486670A1/es not_active Expired
- 1979-12-10 NL NL7908881A patent/NL7908881A/nl active Search and Examination
Also Published As
| Publication number | Publication date |
|---|---|
| US4257976A (en) | 1981-03-24 |
| ES486670A1 (es) | 1980-05-16 |
| DE2949384A1 (de) | 1980-06-26 |
| IT1164774B (it) | 1987-04-15 |
| SE430984B (sv) | 1983-12-27 |
| DE2949384C2 (forum.php) | 1990-09-13 |
| IT7951027A0 (it) | 1979-12-07 |
| BE880490A (fr) | 1980-06-09 |
| CH641751A5 (fr) | 1984-03-15 |
| SE7908765L (sv) | 1980-06-09 |
| JPS56108736A (en) | 1981-08-28 |
| NL7908881A (nl) | 1980-06-10 |
| FR2443452A1 (fr) | 1980-07-04 |
| JPS6410508B2 (forum.php) | 1989-02-22 |
| FR2443452B1 (forum.php) | 1981-08-14 |
| HU181948B (en) | 1983-11-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |