CH664957A5 - Verfahren zur herstellung von 4-hydroxy-2-oxo-pyrrolidin-1-yl-acetamid. - Google Patents
Verfahren zur herstellung von 4-hydroxy-2-oxo-pyrrolidin-1-yl-acetamid. Download PDFInfo
- Publication number
- CH664957A5 CH664957A5 CH412685A CH412685A CH664957A5 CH 664957 A5 CH664957 A5 CH 664957A5 CH 412685 A CH412685 A CH 412685A CH 412685 A CH412685 A CH 412685A CH 664957 A5 CH664957 A5 CH 664957A5
- Authority
- CH
- Switzerland
- Prior art keywords
- oxo
- hydroxy
- alkyl
- acetic acid
- ester
- Prior art date
Links
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910000033 sodium borohydride Inorganic materials 0.000 claims abstract description 5
- 239000012279 sodium borohydride Substances 0.000 claims abstract description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- IHLAQQPQKRMGSS-UHFFFAOYSA-N oxiracetam Chemical compound NC(=O)CN1CC(O)CC1=O IHLAQQPQKRMGSS-UHFFFAOYSA-N 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- DWAWYEUJUWLESO-UHFFFAOYSA-N trichloromethylsilane Chemical compound [SiH3]C(Cl)(Cl)Cl DWAWYEUJUWLESO-UHFFFAOYSA-N 0.000 claims description 5
- -1 2,4-dioxopyrrolidin-l-yl Chemical group 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 3
- 230000009435 amidation Effects 0.000 claims description 3
- 238000007112 amidation reaction Methods 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 235000009518 sodium iodide Nutrition 0.000 claims description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 239000007795 chemical reaction product Substances 0.000 claims 2
- BMOXYLBGPIDAAN-UHFFFAOYSA-N 2-(4-hydroxy-2-oxopyrrolidin-1-yl)acetic acid Chemical compound OC1CN(CC(O)=O)C(=O)C1 BMOXYLBGPIDAAN-UHFFFAOYSA-N 0.000 claims 1
- IOGISYQVOGVIEU-UHFFFAOYSA-N 4-hydroxypyrrolidin-2-one Chemical compound OC1CNC(=O)C1 IOGISYQVOGVIEU-UHFFFAOYSA-N 0.000 claims 1
- MVKLHAOLEIYVRH-UHFFFAOYSA-N C(C)(=O)OCCN1C(C=C(C1)OC)=O Chemical compound C(C)(=O)OCCN1C(C=C(C1)OC)=O MVKLHAOLEIYVRH-UHFFFAOYSA-N 0.000 claims 1
- JUCVMCNRABNRJD-UHFFFAOYSA-N azane;ethyl acetate Chemical compound N.CCOC(C)=O JUCVMCNRABNRJD-UHFFFAOYSA-N 0.000 claims 1
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 abstract 2
- 229910004373 HOAc Inorganic materials 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 229910001516 alkali metal iodide Inorganic materials 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- UTNSRDNJLQQUGX-UHFFFAOYSA-N 2-(2,4-dioxopyrrolidin-1-yl)ethyl acetate Chemical compound CC(=O)OCCN1CC(=O)CC1=O UTNSRDNJLQQUGX-UHFFFAOYSA-N 0.000 description 1
- XBZXYILFISUTDL-UHFFFAOYSA-N 2-(4-hydroxy-2-oxopyrrolidin-1-yl)ethyl acetate Chemical compound CC(=O)OCCN1CC(O)CC1=O XBZXYILFISUTDL-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- LJSRSOQMKIBVRH-UHFFFAOYSA-N ethyl 2-(3-methoxy-5-oxo-2h-pyrrol-1-yl)acetate Chemical compound CCOC(=O)CN1CC(OC)=CC1=O LJSRSOQMKIBVRH-UHFFFAOYSA-N 0.000 description 1
- YDBONCLBTWFUPF-UHFFFAOYSA-N ethyl 2-(4-hydroxy-2-oxopyrrolidin-1-yl)acetate Chemical compound CCOC(=O)CN1CC(O)CC1=O YDBONCLBTWFUPF-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 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)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH412685A CH664957A5 (de) | 1985-09-24 | 1985-09-24 | Verfahren zur herstellung von 4-hydroxy-2-oxo-pyrrolidin-1-yl-acetamid. |
| IL80071A IL80071A0 (en) | 1985-09-24 | 1986-09-17 | Pyrrolidine acetamide derivatives |
| JP22177186A JPS6272661A (ja) | 1985-09-24 | 1986-09-19 | ４−ヒドロキシ−２−オキソ−ピロリジン−１−イル−アセトアミドの製造方法 |
| EP86112952A EP0216325A3 (de) | 1985-09-24 | 1986-09-19 | Verfahren zur Herstellung von 4-Hydroxy-2-oxo-pyrrolidin-1-yl-acetamid |
| NO863769A NO863769L (no) | 1985-09-24 | 1986-09-22 | Fremgangsmaate for fremstilling av 4-hydroksy-2-oksopyrrolin-1-yl-acetamid. |
| ES8602069A ES2001696A6 (es) | 1985-09-24 | 1986-09-22 | Procedimiento para preparar 4-hidroxi-2-oxo-pirrolidin-1-il-acetamida |
| SU864028166A SU1482525A3 (ru) | 1985-09-24 | 1986-09-23 | Способ получени 4-окси-2-оксопирролидин-1-ил-ацетамида |
| DK453586A DK453586A (da) | 1985-09-24 | 1986-09-23 | Fremgangsmaade til fremstilling af 4-hydroxy-2-oxo-pyrrolidin-1-yl-acetamid |
| HU864071A HUT43039A (en) | 1985-09-24 | 1986-09-24 | Process for preparing 4-hydroxy-2-oxo-pyrrolidin-1-yl-acetamide |
| CS866880A CS257294B2 (en) | 1985-09-24 | 1986-09-24 | Productionmethod of 4-hydroxy-2-oxo-pyrrolidin-1-yl-acetamid |
| US07/188,702 US4824966A (en) | 1985-09-24 | 1988-05-04 | Process for the production of 4-hydroxy-2-oxo-pyrrolidin-1-yl acetamide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH412685A CH664957A5 (de) | 1985-09-24 | 1985-09-24 | Verfahren zur herstellung von 4-hydroxy-2-oxo-pyrrolidin-1-yl-acetamid. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH664957A5 true CH664957A5 (de) | 1988-04-15 |
Family
ID=4270309
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH412685A CH664957A5 (de) | 1985-09-24 | 1985-09-24 | Verfahren zur herstellung von 4-hydroxy-2-oxo-pyrrolidin-1-yl-acetamid. |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS6272661A (cs) |
| CH (1) | CH664957A5 (cs) |
| CS (1) | CS257294B2 (cs) |
| SU (1) | SU1482525A3 (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9309749D0 (en) * | 1993-05-12 | 1993-06-23 | Boots Co Plc | Therapeutic agents |
-
1985
- 1985-09-24 CH CH412685A patent/CH664957A5/de not_active IP Right Cessation
-
1986
- 1986-09-19 JP JP22177186A patent/JPS6272661A/ja active Pending
- 1986-09-23 SU SU864028166A patent/SU1482525A3/ru active
- 1986-09-24 CS CS866880A patent/CS257294B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS688086A2 (en) | 1987-09-17 |
| SU1482525A3 (ru) | 1989-05-23 |
| CS257294B2 (en) | 1988-04-15 |
| JPS6272661A (ja) | 1987-04-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |