FI108719B - Menetelmä aminoetyyliglysiinin valmistamiseksi - Google Patents
Menetelmä aminoetyyliglysiinin valmistamiseksi Download PDFInfo
- Publication number
- FI108719B FI108719B FI951131A FI951131A FI108719B FI 108719 B FI108719 B FI 108719B FI 951131 A FI951131 A FI 951131A FI 951131 A FI951131 A FI 951131A FI 108719 B FI108719 B FI 108719B
- Authority
- FI
- Finland
- Prior art keywords
- diaminoethane
- water
- alcohol
- process according
- catalyst
- Prior art date
Links
- PIINGYXNCHTJTF-UHFFFAOYSA-N 2-(2-azaniumylethylamino)acetate Chemical compound NCCNCC(O)=O PIINGYXNCHTJTF-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 238000000034 method Methods 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 14
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims abstract description 14
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- 238000001816 cooling Methods 0.000 claims abstract description 7
- 238000003756 stirring Methods 0.000 claims abstract description 7
- 125000005233 alkylalcohol group Chemical group 0.000 claims abstract description 3
- 239000002904 solvent Substances 0.000 claims abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 39
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- 238000004821 distillation Methods 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 8
- 239000001257 hydrogen Substances 0.000 abstract description 8
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 238000000967 suction filtration Methods 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 5
- MOOYVEVEDVVKGD-UHFFFAOYSA-N oxaldehydic acid;hydrate Chemical compound O.OC(=O)C=O MOOYVEVEDVVKGD-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 235000021395 porridge Nutrition 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000003754 machining Methods 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
- -1 methane Chemical compound 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- PJGOZNKMFPTTNC-UHFFFAOYSA-N methyl 2-(2-aminoethylamino)acetate;dihydrochloride Chemical compound Cl.Cl.COC(=O)CNCCN PJGOZNKMFPTTNC-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
- C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4408530 | 1994-03-14 | ||
| DE4408530A DE4408530A1 (de) | 1994-03-14 | 1994-03-14 | Verfahren zur Herstellung von Aminoethylglycin |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI951131A0 FI951131A0 (fi) | 1995-03-10 |
| FI951131A FI951131A (fi) | 1995-09-15 |
| FI108719B true FI108719B (fi) | 2002-03-15 |
Family
ID=6512695
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI951131A FI108719B (fi) | 1994-03-14 | 1995-03-10 | Menetelmä aminoetyyliglysiinin valmistamiseksi |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5516937A (fr) |
| EP (1) | EP0672647B1 (fr) |
| JP (1) | JP3831421B2 (fr) |
| AT (1) | ATE174326T1 (fr) |
| AU (1) | AU692512B2 (fr) |
| CA (1) | CA2144476C (fr) |
| DE (2) | DE4408530A1 (fr) |
| DK (1) | DK0672647T3 (fr) |
| ES (1) | ES2127426T3 (fr) |
| FI (1) | FI108719B (fr) |
| GR (1) | GR3029488T3 (fr) |
| NO (1) | NO305791B1 (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6919441B2 (en) | 1994-03-14 | 2005-07-19 | Aventis Pharma Deutschland Gmbh | Polyamide-oligonucleotide derivatives, their preparation and use |
| EP2039679B1 (fr) * | 2007-09-20 | 2015-08-12 | Przedsiebiorstwo Produkcyjno-Consultingowe ADOB sp. z o.o. sp. k. | Procédé pour la préparation d'acide N,N'-bis(2-hydroxybenzyl)éthylènediamine-N,N'-diacétique et ses dérivés |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2387735A (en) * | 1941-07-03 | 1945-10-30 | Martin Dennis Company | Method of forming carboxylic amino acids |
| DE3132882A1 (de) * | 1981-08-20 | 1983-03-03 | Cassella Ag, 6000 Frankfurt | Neue piperazinone, ihre herstellung und verwendung |
| JPS58170479A (ja) * | 1982-03-30 | 1983-10-07 | Sanraku Inc | ジペプチダ−ゼ阻害剤 |
| HUT41715A (en) * | 1984-12-28 | 1987-05-28 | Monsanto Co | Process for preparing n-substituted alpha-aminoacids and derivatives thereof |
| US4942226A (en) * | 1988-12-29 | 1990-07-17 | Merck & Co., Inc. | Halogenated pyrimidine nucleosides and their derivatives |
-
1994
- 1994-03-14 DE DE4408530A patent/DE4408530A1/de not_active Withdrawn
-
1995
- 1995-03-08 DK DK95103317T patent/DK0672647T3/da active
- 1995-03-08 DE DE59504455T patent/DE59504455D1/de not_active Expired - Lifetime
- 1995-03-08 ES ES95103317T patent/ES2127426T3/es not_active Expired - Lifetime
- 1995-03-08 AT AT95103317T patent/ATE174326T1/de active
- 1995-03-08 EP EP95103317A patent/EP0672647B1/fr not_active Expired - Lifetime
- 1995-03-10 AU AU14802/95A patent/AU692512B2/en not_active Ceased
- 1995-03-10 FI FI951131A patent/FI108719B/fi not_active IP Right Cessation
- 1995-03-13 US US08/402,383 patent/US5516937A/en not_active Expired - Lifetime
- 1995-03-13 CA CA002144476A patent/CA2144476C/fr not_active Expired - Fee Related
- 1995-03-13 NO NO950956A patent/NO305791B1/no not_active IP Right Cessation
- 1995-03-14 JP JP05464095A patent/JP3831421B2/ja not_active Expired - Fee Related
-
1999
- 1999-02-25 GR GR990400584T patent/GR3029488T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI951131A0 (fi) | 1995-03-10 |
| US5516937A (en) | 1996-05-14 |
| DE4408530A1 (de) | 1995-09-28 |
| NO950956L (no) | 1995-09-15 |
| NO950956D0 (no) | 1995-03-13 |
| ATE174326T1 (de) | 1998-12-15 |
| EP0672647B1 (fr) | 1998-12-09 |
| CA2144476C (fr) | 2005-11-29 |
| CA2144476A1 (fr) | 1995-09-15 |
| FI951131A (fi) | 1995-09-15 |
| GR3029488T3 (en) | 1999-05-28 |
| JP3831421B2 (ja) | 2006-10-11 |
| DE59504455D1 (de) | 1999-01-21 |
| ES2127426T3 (es) | 1999-04-16 |
| DK0672647T3 (da) | 1999-08-16 |
| EP0672647A1 (fr) | 1995-09-20 |
| JPH07258181A (ja) | 1995-10-09 |
| NO305791B1 (no) | 1999-07-26 |
| AU692512B2 (en) | 1998-06-11 |
| AU1480295A (en) | 1995-09-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Reinhold et al. | Synthesis of L-. alpha.-methyldopa from asymmetric intermediates | |
| HU216071B (hu) | Eljárás acil-glicin-származékok előállítására | |
| EP0592643B1 (fr) | Derives de pleuromutiline | |
| KR910000781B1 (ko) | 글리옥실산 및 글리옥실산 유도체의 제조방법 | |
| JPS59184196A (ja) | ホスフイノトリシンの製法 | |
| FI108719B (fi) | Menetelmä aminoetyyliglysiinin valmistamiseksi | |
| JPH03236359A (ja) | 環状アミノ酸抗けいれん性化合物の改良製法 | |
| EP0252353B1 (fr) | 4-Benzyloxy-3-pyrroline-2-one-1-yl-acétamide, préparation et utilisation | |
| US4764614A (en) | Process for preparing (S)(+)-4,4'(methyl-1,2-ethanediyl)-bis(2,6-piperazinedione) | |
| US5110919A (en) | Process for the preparation of 2-amino-9-(2,3,5-tri-o-benzyl-beta-d-arabinofuranosyl) adenine and novel intermediates | |
| US4822895A (en) | 3-aminoazetidine, its salts and intermediates of synthesis | |
| IE911313A1 (en) | "New process for the preparation of 1-(2,3,4-trimethoxybenzyl)piperazine by reductive amination" | |
| US2557041A (en) | Synthesis of tryptophane | |
| US4943679A (en) | Process for the N-ω-trifluoroacetylation of saturated aliphatic monocarboxylic α,ω-diamino acids | |
| US5041637A (en) | Process for the synthesis of optically active aminoacids | |
| HU214942B (hu) | Eljárás N-helyettesített glicin-észterek és glicin, továbbá ezekből indoxil- és indigószármazékok előállítására | |
| EP2269983A1 (fr) | Procédé de production d'une 2-pyrrolidinone N-alkylée | |
| EP0355085B1 (fr) | Procede de preparation de 9-(hydroxyalkyl)-hypoxanthines | |
| EP0053584B1 (fr) | Procédé de résolution de sulpiride racémique | |
| IE64176B1 (en) | Process for the preparation of indolinone-2-derivatives | |
| Laffan et al. | An Efficient Synthesis of Racemic 4‐Hydroxy‐2‐oxo‐1‐pyrrolidineacetamide (Oxiracetam) Using Tetramic‐Acid Intermediates | |
| CN110835319B (zh) | 一种贝那普利中间体和贝那普利盐酸盐的合成方法 | |
| JPH0510332B2 (fr) | ||
| PL209729B1 (pl) | Sposób wytwarzania chlorowodorku 2-[(2,3,4-trihydroksyfenylo)metylo]hydrazydu D,L-seryny | |
| NL8901409A (nl) | Werkwijze voor de bereiding van methyl 3-aminocrotonaat. |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |