FR2491921A1 - Nouveaux esters terbutiliques derives de l'acide 2,2-dimethyl cyclopropane 1,3-dicarboxylique, leur preparation et les nouveaux intermediaires obtenus - Google Patents
Nouveaux esters terbutiliques derives de l'acide 2,2-dimethyl cyclopropane 1,3-dicarboxylique, leur preparation et les nouveaux intermediaires obtenus Download PDFInfo
- Publication number
- FR2491921A1 FR2491921A1 FR8021691A FR8021691A FR2491921A1 FR 2491921 A1 FR2491921 A1 FR 2491921A1 FR 8021691 A FR8021691 A FR 8021691A FR 8021691 A FR8021691 A FR 8021691A FR 2491921 A1 FR2491921 A1 FR 2491921A1
- Authority
- FR
- France
- Prior art keywords
- formula
- compound
- cis
- configuration
- 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.)
- Granted
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 150000002148 esters Chemical class 0.000 title claims description 25
- 239000000543 intermediate Substances 0.000 title description 6
- MSPJNHHBNOLHOC-UHFFFAOYSA-N 3,3-dimethylcyclopropane-1,2-dicarboxylic acid Chemical compound CC1(C)C(C(O)=O)C1C(O)=O MSPJNHHBNOLHOC-UHFFFAOYSA-N 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 58
- 238000000034 method Methods 0.000 claims abstract description 8
- 230000008569 process Effects 0.000 claims abstract description 7
- 239000012374 esterification agent Substances 0.000 claims abstract description 6
- 230000009471 action Effects 0.000 claims abstract description 4
- 125000004492 methyl ester group Chemical group 0.000 claims abstract 3
- 239000002253 acid Substances 0.000 claims description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 7
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- 241001331845 Equus asinus x caballus Species 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 150000004703 alkoxides Chemical class 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 238000006317 isomerization reaction Methods 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- MSPJNHHBNOLHOC-ZXZARUISSA-N (1s,2r)-3,3-dimethylcyclopropane-1,2-dicarboxylic acid Chemical compound CC1(C)[C@H](C(O)=O)[C@@H]1C(O)=O MSPJNHHBNOLHOC-ZXZARUISSA-N 0.000 claims 1
- MSPJNHHBNOLHOC-QWWZWVQMSA-N (1s,2s)-3,3-dimethylcyclopropane-1,2-dicarboxylic acid Chemical compound CC1(C)[C@@H](C(O)=O)[C@@H]1C(O)=O MSPJNHHBNOLHOC-QWWZWVQMSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 150000004702 methyl esters Chemical group 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 230000009466 transformation Effects 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 230000000707 stereoselective effect Effects 0.000 description 4
- PBIJFSCPEFQXBB-UHFFFAOYSA-N 1,1-dimethylcyclopropane Chemical class CC1(C)CC1 PBIJFSCPEFQXBB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 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 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 208000037656 Respiratory Sounds Diseases 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- BFAKENXZKHGIGE-UHFFFAOYSA-N bis(2,3,5,6-tetrafluoro-4-iodophenyl)diazene Chemical compound FC1=C(C(=C(C(=C1F)I)F)F)N=NC1=C(C(=C(C(=C1F)F)I)F)F BFAKENXZKHGIGE-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- FDKLLWKMYAMLIF-UHFFFAOYSA-N cyclopropane-1,1-dicarboxylic acid Chemical class OC(=O)C1(C(O)=O)CC1 FDKLLWKMYAMLIF-UHFFFAOYSA-N 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 206010037833 rales Diseases 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- -1 triphenylisopropyl phosphonium halide Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8021691A FR2491921A1 (fr) | 1980-10-10 | 1980-10-10 | Nouveaux esters terbutiliques derives de l'acide 2,2-dimethyl cyclopropane 1,3-dicarboxylique, leur preparation et les nouveaux intermediaires obtenus |
| DE8181401521T DE3168349D1 (en) | 1980-10-10 | 1981-10-02 | Terbutylester derivatives of 2,2-dimethylcyclopropane-1,3-dicarboxylic acids, their preparation and intermediates obtained |
| EP81401521A EP0050543B1 (fr) | 1980-10-10 | 1981-10-02 | Nouveaux esters terbutyliques dérivés de l'acide 2,2-diméthyl cyclopropane 1,3-dicarboxylique, leur préparation et les nouveaux intermédiaires obtenus |
| AT81401521T ATE11276T1 (de) | 1980-10-10 | 1981-10-02 | Terbutylesterderivate von 2,2-dimethylcyclopropan-1,3-dicarbonsaeure, verfahren zu ihrer herstellung und ihre zwischenprodukte. |
| CA000387685A CA1181415A (fr) | 1980-10-10 | 1981-10-09 | Esters terbutyliques derives de l'acide 2,2-dimethyl cyclopropane 1,3-dicarboxylique, et leur preparation |
| HU812926A HU188148B (en) | 1980-10-10 | 1981-10-09 | Process for preparing tert.butyl-esters of 2,2-dimethyl-cyclopropane-1,3-dicarboxylic acid |
| JP56161090A JPS57126446A (en) | 1980-10-10 | 1981-10-12 | Novel t-butyl ester derived from 2,2-dimethylcyclopropane-1,3-dicarboxylic acid, manufacture and obtained novel intermediate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8021691A FR2491921A1 (fr) | 1980-10-10 | 1980-10-10 | Nouveaux esters terbutiliques derives de l'acide 2,2-dimethyl cyclopropane 1,3-dicarboxylique, leur preparation et les nouveaux intermediaires obtenus |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2491921A1 true FR2491921A1 (fr) | 1982-04-16 |
| FR2491921B1 FR2491921B1 (en, 2012) | 1983-12-30 |
Family
ID=9246751
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8021691A Granted FR2491921A1 (fr) | 1980-10-10 | 1980-10-10 | Nouveaux esters terbutiliques derives de l'acide 2,2-dimethyl cyclopropane 1,3-dicarboxylique, leur preparation et les nouveaux intermediaires obtenus |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0050543B1 (en, 2012) |
| JP (1) | JPS57126446A (en, 2012) |
| AT (1) | ATE11276T1 (en, 2012) |
| CA (1) | CA1181415A (en, 2012) |
| DE (1) | DE3168349D1 (en, 2012) |
| FR (1) | FR2491921A1 (en, 2012) |
| HU (1) | HU188148B (en, 2012) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE862461A (fr) * | 1976-12-30 | 1978-06-29 | Roussel Uclaf | Procede de preparation d'esters d'alcoyle inferieur d'acides cis ou trans 3-formyl cyclopropane 2,2-disubstitues racemiques |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2376119A1 (fr) * | 1976-12-30 | 1978-07-28 | Roussel Uclaf | Procede de preparation d'esters d'alcoyle inferieur d'acides trans cyclopropane-1,3-dicarboxyliques 2,2-disubstitues racemiques et nouveaux esters desdits acides |
-
1980
- 1980-10-10 FR FR8021691A patent/FR2491921A1/fr active Granted
-
1981
- 1981-10-02 EP EP81401521A patent/EP0050543B1/fr not_active Expired
- 1981-10-02 DE DE8181401521T patent/DE3168349D1/de not_active Expired
- 1981-10-02 AT AT81401521T patent/ATE11276T1/de not_active IP Right Cessation
- 1981-10-09 CA CA000387685A patent/CA1181415A/fr not_active Expired
- 1981-10-09 HU HU812926A patent/HU188148B/hu not_active IP Right Cessation
- 1981-10-12 JP JP56161090A patent/JPS57126446A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE862461A (fr) * | 1976-12-30 | 1978-06-29 | Roussel Uclaf | Procede de preparation d'esters d'alcoyle inferieur d'acides cis ou trans 3-formyl cyclopropane 2,2-disubstitues racemiques |
Non-Patent Citations (1)
| Title |
|---|
| CA1970 * |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2491921B1 (en, 2012) | 1983-12-30 |
| JPS57126446A (en) | 1982-08-06 |
| CA1181415A (fr) | 1985-01-22 |
| EP0050543A3 (en) | 1982-09-15 |
| JPH032852B2 (en, 2012) | 1991-01-17 |
| EP0050543B1 (fr) | 1985-01-16 |
| ATE11276T1 (de) | 1985-02-15 |
| DE3168349D1 (en) | 1985-02-28 |
| EP0050543A2 (fr) | 1982-04-28 |
| HU188148B (en) | 1986-03-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |