CH420104A - Verfahren zur Herstellung optisch aktiver Verbindungen - Google Patents
Verfahren zur Herstellung optisch aktiver VerbindungenInfo
- Publication number
- CH420104A CH420104A CH1399962A CH1399962A CH420104A CH 420104 A CH420104 A CH 420104A CH 1399962 A CH1399962 A CH 1399962A CH 1399962 A CH1399962 A CH 1399962A CH 420104 A CH420104 A CH 420104A
- Authority
- CH
- Switzerland
- Prior art keywords
- ester
- methyl
- malonic acid
- optically active
- benzyloxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- YFEJFKLTGBWWPS-UHFFFAOYSA-N 2-methyl-2-phenylmethoxypropanedioic acid Chemical compound OC(=O)C(C(O)=O)(C)OCC1=CC=CC=C1 YFEJFKLTGBWWPS-UHFFFAOYSA-N 0.000 claims description 4
- -1 ester acid chloride Chemical class 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 150000002690 malonic acid derivatives Chemical class 0.000 claims description 3
- 238000004508 fractional distillation Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 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 12
- 239000000243 solution Substances 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- ZJAXMXGTROJZOK-UHFFFAOYSA-N 3-ethoxy-2-methyl-3-oxo-2-phenylmethoxypropanoic acid Chemical compound CCOC(=O)C(C)(C(O)=O)OCC1=CC=CC=C1 ZJAXMXGTROJZOK-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000000926 separation method Methods 0.000 description 5
- BLGXFZZNTVWLAY-SCYLSFHTSA-N yohimbine Chemical class C1=CC=C2C(CCN3C[C@@H]4CC[C@H](O)[C@@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-SCYLSFHTSA-N 0.000 description 5
- ZJAXMXGTROJZOK-CYBMUJFWSA-N (2r)-3-ethoxy-2-methyl-3-oxo-2-phenylmethoxypropanoic acid Chemical compound CCOC(=O)[C@@](C)(C(O)=O)OCC1=CC=CC=C1 ZJAXMXGTROJZOK-CYBMUJFWSA-N 0.000 description 4
- ZJAXMXGTROJZOK-ZDUSSCGKSA-N (2s)-3-ethoxy-2-methyl-3-oxo-2-phenylmethoxypropanoic acid Chemical compound CCOC(=O)[C@](C)(C(O)=O)OCC1=CC=CC=C1 ZJAXMXGTROJZOK-ZDUSSCGKSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 229940093499 ethyl acetate Drugs 0.000 description 4
- 235000019439 ethyl acetate Nutrition 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- DGZVAHBEMUJHNF-UHFFFAOYSA-N Cl.CCOC(=O)C(C)(C(O)=O)OCC1=CC=CC=C1 Chemical compound Cl.CCOC(=O)C(C)(C(O)=O)OCC1=CC=CC=C1 DGZVAHBEMUJHNF-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 239000007832 Na2SO4 Substances 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- QHTRBQBPXGFDDO-UHFFFAOYSA-N 2-bromo-2-methylpropanedioic acid Chemical compound OC(=O)C(Br)(C)C(O)=O QHTRBQBPXGFDDO-UHFFFAOYSA-N 0.000 description 1
- DGZVAHBEMUJHNF-BTQNPOSSSA-N CCOC([C@@](C)(C(O)=O)OCC1=CC=CC=C1)=O.Cl Chemical compound CCOC([C@@](C)(C(O)=O)OCC1=CC=CC=C1)=O.Cl DGZVAHBEMUJHNF-BTQNPOSSSA-N 0.000 description 1
- BLGXFZZNTVWLAY-CCZXDCJGSA-N Yohimbine Natural products C1=CC=C2C(CCN3C[C@@H]4CC[C@@H](O)[C@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-CCZXDCJGSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- BLGXFZZNTVWLAY-UHFFFAOYSA-N beta-Yohimbin Natural products C1=CC=C2C(CCN3CC4CCC(O)C(C4CC33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- AYFIAOGBVMPSAE-UHFFFAOYSA-N diethyl 2-methyl-2-phenylmethoxypropanedioate Chemical compound CCOC(=O)C(C)(C(=O)OCC)OCC1=CC=CC=C1 AYFIAOGBVMPSAE-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229960003133 ergot alkaloid Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- BXRNXXXXHLBUKK-UHFFFAOYSA-N piperazine-2,5-dione Chemical compound O=C1CNC(=O)CN1 BXRNXXXXHLBUKK-UHFFFAOYSA-N 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- LFQULJPVXNYWAG-UHFFFAOYSA-N sodium;phenylmethanolate Chemical compound [Na]OCC1=CC=CC=C1 LFQULJPVXNYWAG-UHFFFAOYSA-N 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229960000317 yohimbine Drugs 0.000 description 1
- AADVZSXPNRLYLV-UHFFFAOYSA-N yohimbine carboxylic acid Natural products C1=CC=C2C(CCN3CC4CCC(C(C4CC33)C(O)=O)O)=C3NC2=C1 AADVZSXPNRLYLV-UHFFFAOYSA-N 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
- C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
- C07C69/38—Malonic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/675—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids of saturated hydroxy-carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH654666A CH454826A (de) | 1962-11-29 | 1962-11-29 | Verfahren zur Herstellung optisch aktiver Verbindungen |
| CH1399962A CH420104A (de) | 1962-11-29 | 1962-11-29 | Verfahren zur Herstellung optisch aktiver Verbindungen |
| SE8134/67A SE307937B (OSRAM) | 1962-11-29 | 1963-07-23 | |
| GB41449/63A GB1059628A (en) | 1962-11-29 | 1963-10-21 | Process for the manufacture of optically active compounds |
| NL300873A NL300873A (OSRAM) | 1962-11-29 | 1963-11-22 | |
| LU44890D LU44890A1 (OSRAM) | 1962-11-29 | 1963-11-27 | |
| AT948363A AT244943B (de) | 1962-11-29 | 1963-11-27 | Verfahren zur optischen Spaltung racemischer 2-Methyl-2-benzyloxymalonsäuremonoalkylester |
| FR955156A FR1389490A (fr) | 1962-11-29 | 1963-11-27 | Procédé de préparation de dérivés optiquement actifs de l'acide malonique |
| US326390A US3294835A (en) | 1962-11-29 | 1963-11-27 | 2-methyl-2-benzyloxymalonic acid monoalkyl esters |
| DK558063AA DK112376B (da) | 1962-11-29 | 1963-11-28 | Fremgangsmåde til opspaltning af racemiske malonsyrederivater i deres optisk aktive komponenter. |
| FI2343/63A FI40281B (OSRAM) | 1962-11-29 | 1963-11-28 | |
| SE13175/63A SE306526B (OSRAM) | 1962-11-29 | 1963-11-28 | |
| ES293976A ES293976A1 (es) | 1962-11-29 | 1963-11-28 | Procedimiento de preparación de derivados ópticamente activos del ácido malónico |
| DK89966AA DK114264B (da) | 1962-11-29 | 1966-02-21 | Fremgangsmåde til opstaltning af racemiske malonsyrederivater i deres optisk aktive komponenter. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1399962A CH420104A (de) | 1962-11-29 | 1962-11-29 | Verfahren zur Herstellung optisch aktiver Verbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH420104A true CH420104A (de) | 1966-09-15 |
Family
ID=4397105
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1399962A CH420104A (de) | 1962-11-29 | 1962-11-29 | Verfahren zur Herstellung optisch aktiver Verbindungen |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3294835A (OSRAM) |
| AT (1) | AT244943B (OSRAM) |
| CH (1) | CH420104A (OSRAM) |
| DK (2) | DK112376B (OSRAM) |
| ES (1) | ES293976A1 (OSRAM) |
| FI (1) | FI40281B (OSRAM) |
| GB (1) | GB1059628A (OSRAM) |
| LU (1) | LU44890A1 (OSRAM) |
| NL (1) | NL300873A (OSRAM) |
| SE (2) | SE307937B (OSRAM) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1245982B (de) * | 1964-07-09 | 1967-08-03 | Farbwerke Hoechst Aktiengesellschaft vormals Meister Lucius &. Brüning, Frankfurt/M | Verfahren zur Herstellung von L(-)-B-(3,4-Dihydroxy-phenyl)-a-methyl-alanin |
-
1962
- 1962-11-29 CH CH1399962A patent/CH420104A/de unknown
-
1963
- 1963-07-23 SE SE8134/67A patent/SE307937B/xx unknown
- 1963-10-21 GB GB41449/63A patent/GB1059628A/en not_active Expired
- 1963-11-22 NL NL300873A patent/NL300873A/xx unknown
- 1963-11-27 AT AT948363A patent/AT244943B/de active
- 1963-11-27 US US326390A patent/US3294835A/en not_active Expired - Lifetime
- 1963-11-27 LU LU44890D patent/LU44890A1/xx unknown
- 1963-11-28 SE SE13175/63A patent/SE306526B/xx unknown
- 1963-11-28 FI FI2343/63A patent/FI40281B/fi active
- 1963-11-28 DK DK558063AA patent/DK112376B/da unknown
- 1963-11-28 ES ES293976A patent/ES293976A1/es not_active Expired
-
1966
- 1966-02-21 DK DK89966AA patent/DK114264B/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK114264B (da) | 1969-06-16 |
| NL300873A (OSRAM) | 1965-09-27 |
| US3294835A (en) | 1966-12-27 |
| ES293976A1 (es) | 1964-05-16 |
| SE307937B (OSRAM) | 1969-01-27 |
| FI40281B (OSRAM) | 1968-09-02 |
| AT244943B (de) | 1966-02-10 |
| LU44890A1 (OSRAM) | 1964-05-27 |
| GB1059628A (en) | 1967-02-22 |
| SE306526B (OSRAM) | 1968-12-02 |
| DK112376B (da) | 1968-12-09 |
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