JPS6410508B2 - - Google Patents
Info
- Publication number
- JPS6410508B2 JPS6410508B2 JP54158226A JP15822679A JPS6410508B2 JP S6410508 B2 JPS6410508 B2 JP S6410508B2 JP 54158226 A JP54158226 A JP 54158226A JP 15822679 A JP15822679 A JP 15822679A JP S6410508 B2 JPS6410508 B2 JP S6410508B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- chrysanthemum
- cis
- salt
- trans
- 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
- 239000002253 acid Substances 0.000 claims description 104
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 32
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 18
- 241000723353 Chrysanthemum Species 0.000 claims description 15
- 235000007516 Chrysanthemum Nutrition 0.000 claims description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 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 5
- 238000002425 crystallisation Methods 0.000 claims description 5
- 230000008025 crystallization Effects 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 239000012452 mother liquor Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- FMCGSUUBYTWNDP-ONGXEEELSA-N (1R,2S)-2-(dimethylamino)-1-phenyl-1-propanol Chemical class CN(C)[C@@H](C)[C@H](O)C1=CC=CC=C1 FMCGSUUBYTWNDP-ONGXEEELSA-N 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- 239000007788 liquid Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000010908 decantation Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- FMCGSUUBYTWNDP-UHFFFAOYSA-N Methylephedrine Chemical compound CN(C)C(C)C(O)C1=CC=CC=C1 FMCGSUUBYTWNDP-UHFFFAOYSA-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
- 150000007513 acids Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229960002179 ephedrine Drugs 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 1
- 235000001258 Cinchona calisaya Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 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
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229940073569 n-methylephedrine Drugs 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005406 washing 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7834591A FR2443452A1 (fr) | 1978-12-08 | 1978-12-08 | Nouveau procede de dedoublement de l'acide dl cis et dl trans chrysanthemique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56108736A JPS56108736A (en) | 1981-08-28 |
| JPS6410508B2 true JPS6410508B2 (en, 2012) | 1989-02-22 |
Family
ID=9215840
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15822679A Granted JPS56108736A (en) | 1978-12-08 | 1979-12-07 | Novel resolution of dllciss and dlltransschrysanthemic acid |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4257976A (en, 2012) |
| JP (1) | JPS56108736A (en, 2012) |
| BE (1) | BE880490A (en, 2012) |
| CA (1) | CA1127180A (en, 2012) |
| CH (1) | CH641751A5 (en, 2012) |
| DE (1) | DE2949384A1 (en, 2012) |
| ES (1) | ES486670A1 (en, 2012) |
| FR (1) | FR2443452A1 (en, 2012) |
| HU (1) | HU181948B (en, 2012) |
| IT (1) | IT1164774B (en, 2012) |
| NL (1) | NL7908881A (en, 2012) |
| SE (1) | SE430984B (en, 2012) |
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 |
| WO1993025667A1 (en) * | 1992-06-05 | 1993-12-23 | The Scripps Research Institute | D-enzyme compositions and methods of their use |
| 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 |
| CH486411A (de) * | 1966-04-27 | 1970-02-28 | Sumitomo Chemical Co | Verfahren zur Herstellung von optisch hochreinem (+)-trans-Chrysanthemummonocarbonsäure-Chininsalz |
| 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 (en, 2012) * | 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 (en, 2012) * | 1972-01-07 | 1976-07-17 | ||
| JPS4992049A (en, 2012) * | 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 DE DE19792949384 patent/DE2949384A1/de active Granted
- 1979-12-07 ES ES486670A patent/ES486670A1/es not_active Expired
- 1979-12-07 CH CH1087779A patent/CH641751A5/fr not_active IP Right Cessation
- 1979-12-07 BE BE0/198472A patent/BE880490A/fr not_active IP Right Cessation
- 1979-12-07 IT IT51027/79A patent/IT1164774B/it active
- 1979-12-07 JP JP15822679A patent/JPS56108736A/ja active Granted
- 1979-12-10 NL NL7908881A patent/NL7908881A/nl active Search and Examination
Also Published As
| Publication number | Publication date |
|---|---|
| DE2949384A1 (de) | 1980-06-26 |
| ES486670A1 (es) | 1980-05-16 |
| DE2949384C2 (en, 2012) | 1990-09-13 |
| US4257976A (en) | 1981-03-24 |
| IT1164774B (it) | 1987-04-15 |
| SE430984B (sv) | 1983-12-27 |
| SE7908765L (sv) | 1980-06-09 |
| FR2443452B1 (en, 2012) | 1981-08-14 |
| CA1127180A (fr) | 1982-07-06 |
| JPS56108736A (en) | 1981-08-28 |
| IT7951027A0 (it) | 1979-12-07 |
| HU181948B (en) | 1983-11-28 |
| NL7908881A (nl) | 1980-06-10 |
| BE880490A (fr) | 1980-06-09 |
| CH641751A5 (fr) | 1984-03-15 |
| FR2443452A1 (fr) | 1980-07-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS6410508B2 (en, 2012) | ||
| JPS61293949A (ja) | ａ−イソプロピル−ｐ−クロルフエニル酢酸の光学分割法 | |
| US3996246A (en) | Resolution of racemic pantolactone | |
| US4284797A (en) | Process for separating mixtures of 3- and 4-nitrophthalic acid | |
| JPS6213942B2 (en, 2012) | ||
| JPH0314818B2 (en, 2012) | ||
| EP0382506B1 (en) | Optically active diastereomer salts of tetrahydro-2-furoic acid | |
| JPH0395127A (ja) | カルボン酸のラセミ化法 | |
| JPS5838414B2 (ja) | シクロペンテノロン ノ ブンカツホウ | |
| US4127607A (en) | Process for the preparation of an acetamide derivative | |
| JPH0759555B2 (ja) | 光学活性なオキソ―イソインドリニル誘導体の製法 | |
| JP2576598B2 (ja) | 光学活性１−メチル−３−フェニルプロピルアミンの製法 | |
| JPH0570461A (ja) | イソキノリン化合物の製造法 | |
| JPH0374384A (ja) | ３ｒ‐（３‐カルボキシベンジル）‐６‐（５‐フルオロ‐２‐ベンゾチアゾリル）メトキシ‐４ｒ‐クロマノールの光学分割方法 | |
| US2463989A (en) | Preparation of acylated amino esters | |
| US2806859A (en) | L-glutamine synthesis | |
| JP3959798B2 (ja) | １−（３−メトキシフェニル）エチルアミンの光学分割方法 | |
| JPH03261743A (ja) | ジャスモン酸の光学分割方法 | |
| SU278684A1 (ru) | Способ получения n-a1i,hjiamhaa алифатического или ароматического ряда | |
| JPS5832872A (ja) | ベンゾチアゼピン誘導体の光学分割法 | |
| FR2560872A1 (fr) | Procede utilisant un seul solvant pour la preparation d'esters de 3,5-dibromo-4-hydroxybenzonitrile | |
| IE911917A1 (en) | Process for racemate resolution of 2,2-dimethylcyclopropanecarboxylic acid | |
| JPS6041637A (ja) | ｃｉｓ−菊酸アルキルエステルの製造方法及びこれより得られる新規化合物 | |
| JPS63139181A (ja) | ２−（１０，１１−ジヒドロ−１０−オキソジベンゾ〔ｂ，ｆ〕チエピン−２−イル）プロピオン酸の結晶化方法 | |
| BE633582A (en, 2012) |