CH668066A5 - Verfahren zur herstellung von 4-alkoxy-3-pyrrolin-2-on-1-yl-essigsaeureester. - Google Patents
Verfahren zur herstellung von 4-alkoxy-3-pyrrolin-2-on-1-yl-essigsaeureester. Download PDFInfo
- Publication number
- CH668066A5 CH668066A5 CH1958/86A CH195886A CH668066A5 CH 668066 A5 CH668066 A5 CH 668066A5 CH 1958/86 A CH1958/86 A CH 1958/86A CH 195886 A CH195886 A CH 195886A CH 668066 A5 CH668066 A5 CH 668066A5
- Authority
- CH
- Switzerland
- Prior art keywords
- alkyl
- alkoxy
- ester
- oxo
- pyrroline
- Prior art date
Links
- 125000000217 alkyl group Chemical group 0.000 title abstract 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 239000000010 aprotic solvent Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000003586 protic polar solvent Substances 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 150000003510 tertiary aliphatic amines Chemical class 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- -1 benzyl ester Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000004471 Glycine Substances 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- FCPNSEAKHSMNCT-UHFFFAOYSA-N 2-(3-methoxy-5-oxo-2h-pyrrol-1-yl)acetic acid Chemical compound COC1=CC(=O)N(CC(O)=O)C1 FCPNSEAKHSMNCT-UHFFFAOYSA-N 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- COQRGFWWJBEXRC-UHFFFAOYSA-N hydron;methyl 2-aminoacetate;chloride Chemical compound Cl.COC(=O)CN COQRGFWWJBEXRC-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- IHLAQQPQKRMGSS-UHFFFAOYSA-N oxiracetam Chemical compound NC(=O)CN1CC(O)CC1=O IHLAQQPQKRMGSS-UHFFFAOYSA-N 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/38—2-Pyrrolones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1958/86A CH668066A5 (de) | 1986-05-14 | 1986-05-14 | Verfahren zur herstellung von 4-alkoxy-3-pyrrolin-2-on-1-yl-essigsaeureester. |
| HU863310A HU195773B (en) | 1985-09-24 | 1986-08-01 | Process for preparing alkyl esters of 4-alkoxy-3-pyrrolin-2-on-1-yl-acetic acid |
| IE216186A IE59030B1 (en) | 1985-09-24 | 1986-08-11 | 4-alkoxy-3-pyrrolin-2-on-1-ylacetic acid alkyl esters and process for the preparation thereof |
| CS76790A CS274704B2 (en) | 1986-05-14 | 1986-08-14 | Method of 4-alkoxy-3-pyrroline-2-on-1-yl acetic acid's alkyl esters production |
| IL8679947A IL79947A (en) | 1985-09-24 | 1986-09-04 | 4-alkoxy-3-pyrrolin-2-on-1-yl acetic acid esters and process for their preparation |
| EP86112951A EP0216324B1 (de) | 1985-09-24 | 1986-09-19 | 4-Alkoxy-3-pyrrolin-2-on-1-yl-essigsäurealkyl- bzw. -benzylester sowie deren Herstellung |
| AT86112951T ATE58527T1 (de) | 1985-09-24 | 1986-09-19 | 4-alkoxy-3-pyrrolin-2-on-1-yl-essigsaeurealkylbzw. -benzylester sowie deren herstellung. |
| DE8686112951T DE3675722D1 (de) | 1985-09-24 | 1986-09-19 | 4-alkoxy-3-pyrrolin-2-on-1-yl-essigsaeurealkyl- bzw. -benzylester sowie deren herstellung. |
| JP61221770A JPH0742269B2 (ja) | 1985-09-24 | 1986-09-19 | ４−アルコキシ−３−ピロリン−２−オン−１−イル−酢酸アルキルエステルおよびその製造方法 |
| ES8602068A ES2001695A6 (es) | 1985-09-24 | 1986-09-22 | Procedimiento para preparar esteres alquilicos de c1-c4 de acido 4-alcoxi-3-pirrolin-2-on-1-il-acetico |
| DK453486A DK453486A (da) | 1985-09-24 | 1986-09-23 | 4-alkoxy-3-pyrrolin-2-on-1-yl-eddikesyre-alkylestere samt deres fremstilling |
| NO86863791A NO171848C (no) | 1985-09-24 | 1986-09-23 | Fremstilling av 4-alkoksy-3-pyrrolin-2-on-1-yl-eddiksyrealkylestere |
| CA000519007A CA1271769A (en) | 1985-09-24 | 1986-09-24 | 4-alkoxy-3-pyrrolin-2-on-1-yl acetic acid alkyl esters and their production |
| US06/931,849 US4780545A (en) | 1985-09-24 | 1986-11-18 | Production of 4-alkoxy-3-pyrrolin-2-on-1-yl acetic acid alkyl esters |
| SU874203443A SU1486057A3 (ru) | 1986-05-14 | 1987-10-12 | СПОСОБ ПОЛУЧЕНИЯ С ,,-С4-АЛКИЛОВЫХ ЭФИРОВ 4-АЛКОКСИ-3-ПИРРОЛИН-2—ОН—1— ИЛУКСУСНОЙ кислоты. |
| US07/147,275 US4880940A (en) | 1985-09-24 | 1988-07-22 | 4-alkoxy-3-pyrrolin-2-on-1-yl acetic acid alkyl esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1958/86A CH668066A5 (de) | 1986-05-14 | 1986-05-14 | Verfahren zur herstellung von 4-alkoxy-3-pyrrolin-2-on-1-yl-essigsaeureester. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH668066A5 true CH668066A5 (de) | 1988-11-30 |
Family
ID=4222573
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1958/86A CH668066A5 (de) | 1985-09-24 | 1986-05-14 | Verfahren zur herstellung von 4-alkoxy-3-pyrrolin-2-on-1-yl-essigsaeureester. |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH668066A5 (cs) |
| CS (1) | CS274704B2 (cs) |
| SU (1) | SU1486057A3 (cs) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5276164A (en) * | 1990-06-26 | 1994-01-04 | Lonza Ltd. | Process for the production of 4-hydroxy-2-oxopyrrolidin-1-yl-acetamide |
-
1986
- 1986-05-14 CH CH1958/86A patent/CH668066A5/de not_active IP Right Cessation
- 1986-08-14 CS CS76790A patent/CS274704B2/cs unknown
-
1987
- 1987-10-12 SU SU874203443A patent/SU1486057A3/ru active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5276164A (en) * | 1990-06-26 | 1994-01-04 | Lonza Ltd. | Process for the production of 4-hydroxy-2-oxopyrrolidin-1-yl-acetamide |
| US5371237A (en) * | 1990-06-26 | 1994-12-06 | Lonza Ltd. | Process for the production of 4-hydroxy-2-oxopyrrolidin-1-yl-acetamide |
Also Published As
| Publication number | Publication date |
|---|---|
| CS76790A2 (en) | 1990-11-14 |
| SU1486057A3 (ru) | 1989-06-07 |
| CS274704B2 (en) | 1991-09-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |