SI9420074B - Postopek za pripravo N-substituiranih glicinskih kislin ali glicin estrov in uporaba tega postopka za sintezo indiga - Google Patents
Postopek za pripravo N-substituiranih glicinskih kislin ali glicin estrov in uporaba tega postopka za sintezo indiga Download PDFInfo
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- SI9420074B SI9420074B SI9420074A SI9420074A SI9420074B SI 9420074 B SI9420074 B SI 9420074B SI 9420074 A SI9420074 A SI 9420074A SI 9420074 A SI9420074 A SI 9420074A SI 9420074 B SI9420074 B SI 9420074B
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Classifications
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07C229/14—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of carbon skeletons containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/18—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/36—Oxygen atoms in position 3, e.g. adrenochrome
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pyrrole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Claims (10)
1 PATENTNI ZAHTEVKI 1. Postopek za pripravo N-substituiranega glicin estra ali N-substituirane glicinske kisline s formulo RiR2N-CH2-COOR I v kateri R pomeni ravnoverižno ali razvejeno alkilno skupino z 1 do 10 atomi C ter R! in R2 neodvisno eden od drugega pomenita vodik, nesubstituirano ali s halogenom, z alkilnimi skupinami z 1 do 6 atomi C ali z alkoksi skupinami z 1 do 4 atomi C substituirano fenilno ali naftilno skupino, ali ravnoverižno, razvejeno ali ciklično alkilno skupino z 1 do 22 atomi C, ki je lahko nesubstituirana ali substituirana z alkoksi skupinami z 1 do 4 atomi C ali fenilnimi skupinami, pri čemer Ri in R2 ne pomenita istočasno vodik, označen s tem, da polacetal estra glioksilne kisline s formulo R30(0H)CH-C00R II v kateri ima R zgoraj navedeni pomen in R3 pomeni alkilno skupino z 1 do 4 atomi C, presnovimo z aminom s formulo R1R2NH III v kateri imata Ri in R2 zgoraj navedeni pomen, v razredčilu pri temperaturah od 0 °C do temperature refluksa uporabljenega razredčila in nastali vmesni produkt obdelamo v prisotnosti katalizatorja za hidrogeniranje in razredčila z vodikom pod tlakom, pri čemer nastane N-substituirani glicin ester s formulo I, ki ga, če je želeno, izoliramo iz reakcijske zmesi in po izbiri pretvorimo v sol ali v prosto kislino. 2.
2. Postopek po zahtevku 1, označen s tem, da uporabimo spojino s formulo II, v kateri sta R in R3 enaka in pomenita alkilne skupine z 1 do 4 atomi C.
3. Postopek po enem od zahtevkov 1 ali 2, označen s tem, da uporabimo spojino s formulo III, v kateri R! pomeni nesubstituirano ali s halogenom, z alkilnimi skupinami z 1 do 6 atomi C ali z alkoksi skupinami z 1 do 4 atomi C substituirano fenilno ali naftilno skupino in R2 pomeni vodik.
4. Postopek po enem od zahtevkov od 1 do 3 označen s tem, da vzdržujemo pri hidrogenolizi tlak od 4,0 χ 106 Pa do 8,0 χ 106 Pa in temperaturo od 20 °C do 130 °C.
5. Postopek po enem od zahtevkov od 1 do 4, označen s tem, da uporabimo spojino s formulo III, v kateri Ri pomeni nesubstituirano ali z alkilnimi skupinami z 1 do 4 atomi C substituirano fenilno ali naftilno skupino in R2 pomeni vodik.
6. Postopek po enem izmed zahtevkov od 1 do 5, označen s tem, da uporabimo na en mol spojine II od 1 mol do 1,5 mol spojine s formulo III.
7. Postopek po enem od zahtevkov od 1 do 6, označen s tem, da kot razredčilo uporabimo alifatski alkohol z 1 do 4 atomi C, katerega alkilni del ustreza alkilnim delom v uporabljenem polacetalu estra glioksilne kisline.
8. Postopek za pripravo derivata indoksila s formulo % Rt
H iv, 5 v kateri pomenijo R4, R5, in R7 neodvisno eden od drugega vodik, halogen, alkilne skupine z 1 do 6 atomi C ali alkoksi skupine z 1 do 4 atomi C, ali R5 in R^ ali R$ in R7 skupaj vsakokrat z obema atomoma C, na katerih sta substituirana, pomenita nesubstituiran ali s halogenom, z alkilnimi skupinami z 1 do 6 atomi C ali z alkoksi skupinami z 1 do 4 atomi C substituiran benzenski obroč, označen s tem, da N-arilglicin ester s formulo
v kateri ima R v formuli I po zahtevku 1 navedeni pomen in imajo R4, R5, R$ in R7 zgoraj navedene pomene, pripravimo po enem od zahtevkov od 1 do 6, in v prisotnosti staljenega alkalijskega ali zemeljskoalkalijskega hidroksida ob dodatku alkalijskega amida ali brez pri temperaturah od 150 °C do 300 °C sklenemo obroč v indoksil s formulo IV.
9. Postopek po zahtevku 8, označen s tem, da uporabimo N-arilglicin ester s formulo la, v kateri R pomeni alkilno skupino z 1 do 4 atomi C in R4, R5, R$ in R7 neodvisno eden od drugega pomenijo vodik, halogen, alkilne skupine z 1 do 4 atomi C ali alkoksi skupine z 1 do 4 atomi C.
10. Postopek za pripravo derivata indiga s formulo
ο R? Η I ^ /k v. 'R S R H v kateri imajo R4, R5, in R7 v formuli IV po zahtevku 8 navedeni pomen, označen s tem, da derivat indoksila s formulo IV po zahtevku 8 pripravimo po zahtevku 8 in na običajen način oksidiramo v derivat indiga s formulo V.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT0262593A AT401930B (de) | 1993-12-27 | 1993-12-27 | Verfahren zur herstellung von n-substituierten glycinestern und verfahren zur indigosynthese aus den so hergestellten glycinestern |
| DE4403829A DE4403829A1 (de) | 1993-12-27 | 1994-02-08 | Verfahren zur Herstellung von N-substituierten Glycinestern und Verwendung des Verfahrens zur Indigosynthese |
| PCT/EP1994/004259 WO1995018093A1 (de) | 1993-12-27 | 1994-12-21 | Verfahren zur herstellung von n-substituierten glycinsäuren oder glycinestern und verwendung des verfahrens zur indigosynthese |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SI9420074A SI9420074A (en) | 1997-02-28 |
| SI9420074B true SI9420074B (sl) | 2004-02-29 |
Family
ID=49381599
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI9420074A SI9420074B (sl) | 1993-12-27 | 1994-12-21 | Postopek za pripravo N-substituiranih glicinskih kislin ali glicin estrov in uporaba tega postopka za sintezo indiga |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US5686625A (sl) |
| EP (1) | EP0738258B1 (sl) |
| JP (1) | JP3261503B2 (sl) |
| KR (2) | KR100381450B1 (sl) |
| CN (3) | CN1187329C (sl) |
| AT (2) | AT401930B (sl) |
| AU (1) | AU680096B2 (sl) |
| BR (1) | BR9408448A (sl) |
| CA (1) | CA2180101C (sl) |
| CZ (1) | CZ291026B6 (sl) |
| DE (2) | DE4403829A1 (sl) |
| DK (1) | DK0738258T3 (sl) |
| ES (1) | ES2135693T3 (sl) |
| GR (1) | GR3030872T3 (sl) |
| HU (1) | HU214942B (sl) |
| PL (1) | PL181513B1 (sl) |
| SI (1) | SI9420074B (sl) |
| SK (1) | SK282297B6 (sl) |
| WO (1) | WO1995018093A1 (sl) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19604707A1 (de) * | 1996-02-09 | 1997-08-14 | Hoechst Ag | Verfahren zur Herstellung von N-Carboxymethylenanthranilsäure-Estern |
| US6001781A (en) * | 1997-09-10 | 1999-12-14 | The Lubrizol Corporation | Process for preparing condensation product of hydroxy-substituted aromatic compounds and glyoxylic reactants |
| US6864210B2 (en) * | 2003-02-06 | 2005-03-08 | Equistar Chemicals, Lp | Bimetallic olefin polymerization catalysts containing indigoid ligands |
| WO2011115687A2 (en) * | 2010-03-19 | 2011-09-22 | Northwestern University | Alkylated sp-b peptoid compounds and related lung surfactant compositions |
| CN103992241B (zh) * | 2014-06-05 | 2016-08-24 | 雅本化学股份有限公司 | N-取代苯基甘氨酸的制备方法 |
| CN105254517B (zh) * | 2015-09-30 | 2017-08-25 | 上海安诺其集团股份有限公司 | 一种萘环化合物及其制备方法 |
| CA3001065A1 (en) | 2015-10-14 | 2017-04-20 | Xiaoxi WEI | Compositions and methods for reducing ice crystal formation |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB190519353A (en) * | 1905-09-25 | 1906-08-30 | Arthur George Bloxam | Improved Manufacture of Indigo from Phenylglycine or its Derivatives. |
| US2777873A (en) * | 1954-07-01 | 1957-01-15 | Eastman Kodak Co | Preparation of esters of omega-amino acids |
| CH365385A (de) * | 1958-01-13 | 1962-11-15 | Geigy Ag J R | Verfahren zur Herstellung von a-substituierten Glycinen bzw. Glycinestern |
| US4073804A (en) * | 1976-05-04 | 1978-02-14 | Boise Cascade Corporation | Producing glycine by the reductive amination of glyoxylic acid |
| DE3010511A1 (de) * | 1980-03-19 | 1981-10-01 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von alkalisalzen des phenylglycins |
| DE3224795A1 (de) * | 1982-07-02 | 1984-01-05 | Lentia GmbH Chem. u. pharm. Erzeugnisse - Industriebedarf, 8000 München | Verfahren zur herstellung von glyoxylsaeure und glyoxylsaeurederivaten |
| JPS6463557A (en) * | 1987-09-02 | 1989-03-09 | Agency Ind Science Techn | Production of glycine derivative |
-
1993
- 1993-12-27 AT AT0262593A patent/AT401930B/de not_active IP Right Cessation
-
1994
- 1994-02-08 DE DE4403829A patent/DE4403829A1/de not_active Withdrawn
- 1994-12-21 DK DK95905570T patent/DK0738258T3/da active
- 1994-12-21 CN CNB011043369A patent/CN1187329C/zh not_active Expired - Fee Related
- 1994-12-21 HU HU9601758A patent/HU214942B/hu not_active IP Right Cessation
- 1994-12-21 AU AU14141/95A patent/AU680096B2/en not_active Ceased
- 1994-12-21 ES ES95905570T patent/ES2135693T3/es not_active Expired - Lifetime
- 1994-12-21 CZ CZ19961845A patent/CZ291026B6/cs not_active IP Right Cessation
- 1994-12-21 AT AT95905570T patent/ATE182579T1/de not_active IP Right Cessation
- 1994-12-21 CA CA002180101A patent/CA2180101C/en not_active Expired - Fee Related
- 1994-12-21 PL PL94315199A patent/PL181513B1/pl not_active IP Right Cessation
- 1994-12-21 SK SK833-96A patent/SK282297B6/sk not_active IP Right Cessation
- 1994-12-21 US US08/652,445 patent/US5686625A/en not_active Expired - Fee Related
- 1994-12-21 CN CNB011043350A patent/CN1187328C/zh not_active Expired - Fee Related
- 1994-12-21 WO PCT/EP1994/004259 patent/WO1995018093A1/de active IP Right Grant
- 1994-12-21 JP JP51776795A patent/JP3261503B2/ja not_active Expired - Fee Related
- 1994-12-21 KR KR10-2001-7016237A patent/KR100381450B1/ko not_active IP Right Cessation
- 1994-12-21 KR KR1019960703544A patent/KR100368443B1/ko not_active IP Right Cessation
- 1994-12-21 CN CN94194882A patent/CN1091097C/zh not_active Expired - Fee Related
- 1994-12-21 DE DE59408553T patent/DE59408553D1/de not_active Expired - Fee Related
- 1994-12-21 BR BR9408448A patent/BR9408448A/pt not_active IP Right Cessation
- 1994-12-21 EP EP95905570A patent/EP0738258B1/de not_active Expired - Lifetime
- 1994-12-21 SI SI9420074A patent/SI9420074B/sl not_active IP Right Cessation
-
1999
- 1999-07-29 GR GR990401159T patent/GR3030872T3/el unknown
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| Date | Code | Title | Description |
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| IF | Valid on the event date | ||
| KO00 | Lapse of patent |
Effective date: 20100816 |