FI59398C - Foerfarande foer framstaellning av penicillamin och dess homologer - Google Patents
Foerfarande foer framstaellning av penicillamin och dess homologer Download PDFInfo
- Publication number
- FI59398C FI59398C FI2867/72A FI286772A FI59398C FI 59398 C FI59398 C FI 59398C FI 2867/72 A FI2867/72 A FI 2867/72A FI 286772 A FI286772 A FI 286772A FI 59398 C FI59398 C FI 59398C
- Authority
- FI
- Finland
- Prior art keywords
- isopropyl
- thiazolidine
- temperature
- reaction mixture
- dimethylthiazolidine
- Prior art date
Links
- VVNCNSJFMMFHPL-VKHMYHEASA-N D-penicillamine Chemical compound CC(C)(S)[C@@H](N)C(O)=O VVNCNSJFMMFHPL-VKHMYHEASA-N 0.000 title description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 38
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 18
- 150000002825 nitriles Chemical class 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- -1 brine amine Chemical class 0.000 description 8
- 230000007062 hydrolysis Effects 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 125000005521 carbonamide group Chemical group 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- LJRDOKAZOAKLDU-UDXJMMFXSA-N (2s,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-[(2r,3s,4r,5s)-5-[(1r,2r,3s,5r,6s)-3,5-diamino-2-[(2s,3r,4r,5s,6r)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyoxane-3,4-diol;sulfuric ac Chemical compound OS(O)(=O)=O.N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)O[C@@H]1CO LJRDOKAZOAKLDU-UDXJMMFXSA-N 0.000 description 2
- QMUBCEKNQQFXAP-UHFFFAOYSA-N 1,3-thiazolidin-3-ium-3-carboxylate Chemical class OC(=O)N1CCSC1 QMUBCEKNQQFXAP-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N alpha-isobutyric acid Natural products CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229960001639 penicillamine Drugs 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- UEHKBJZDQOQOLX-UHFFFAOYSA-N 5,5-dimethyl-2-propan-2-yl-1,3-thiazolidine Chemical compound CC(C)C1NCC(C)(C)S1 UEHKBJZDQOQOLX-UHFFFAOYSA-N 0.000 description 1
- HHQSUSGDCHSDTO-UHFFFAOYSA-N 5,5-dimethyl-2-propan-2-yl-4h-1,3-thiazole Chemical compound CC(C)C1=NCC(C)(C)S1 HHQSUSGDCHSDTO-UHFFFAOYSA-N 0.000 description 1
- VEKORHIUCKLURX-UHFFFAOYSA-N C(C)(C)C1(SC(CN1)(C)C)C#N Chemical compound C(C)(C)C1(SC(CN1)(C)C)C#N VEKORHIUCKLURX-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000003549 thiazolines Chemical class 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D277/06—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/10—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2156601A DE2156601C3 (de) | 1971-11-15 | 1971-11-15 | Verfahren zur Herstellung von DX-PeniciUamin |
| DE2156601 | 1971-11-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI59398B FI59398B (fi) | 1981-04-30 |
| FI59398C true FI59398C (fi) | 1981-08-10 |
Family
ID=5825136
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI2867/72A FI59398C (fi) | 1971-11-15 | 1972-10-17 | Foerfarande foer framstaellning av penicillamin och dess homologer |
Country Status (21)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU715018A3 (ru) * | 1976-10-09 | 1980-02-05 | Дегусса (Фирма) | Способ получени -цистеина |
| DE2716476C2 (de) * | 1977-04-14 | 1985-07-11 | Robert Bosch Gmbh, 7000 Stuttgart | Niveauregeleinrichtung für Kraftfahrzeuge |
| JPS57195391U (enrdf_load_stackoverflow) * | 1981-06-05 | 1982-12-10 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH540234A (de) * | 1968-09-06 | 1973-08-15 | Degussa | Verfahren zur Herstellung von Penicillamin |
| JPS584587B2 (ja) * | 1977-06-14 | 1983-01-27 | 松下電器産業株式会社 | 回転式粘性剤塗布方法およびその装置 |
-
0
- BE BE791411D patent/BE791411R/xx active
-
1971
- 1971-11-15 DE DE2156601A patent/DE2156601C3/de not_active Expired
- 1971-12-30 SE SE7116964A patent/SE405354B/xx unknown
-
1972
- 1972-10-10 NL NLAANVRAGE7213689,A patent/NL175913C/xx active Search and Examination
- 1972-10-17 FI FI2867/72A patent/FI59398C/fi active
- 1972-10-18 YU YU2599/72A patent/YU39600B/xx unknown
- 1972-10-24 ZA ZA727545A patent/ZA727545B/xx unknown
- 1972-10-25 NO NO3846/72A patent/NO136193C/no unknown
- 1972-10-25 ES ES407956A patent/ES407956A2/es not_active Expired
- 1972-11-01 GB GB5037572A patent/GB1394845A/en not_active Expired
- 1972-11-10 IE IE1537/72A patent/IE36829B1/xx unknown
- 1972-11-10 DK DK559972A patent/DK145624C/da not_active IP Right Cessation
- 1972-11-11 EG EG458/72A patent/EG10782A/xx active
- 1972-11-13 CH CH1648372A patent/CH587240A5/xx not_active IP Right Cessation
- 1972-11-13 IT IT53994/72A patent/IT1045669B/it active
- 1972-11-13 DD DD166822A patent/DD101391A6/xx unknown
- 1972-11-13 AU AU48812/72A patent/AU472713B2/en not_active Expired
- 1972-11-14 IL IL40829A patent/IL40829A/xx unknown
- 1972-11-14 JP JP11419972A patent/JPS566992B2/ja not_active Expired
- 1972-11-14 CS CS727709A patent/CS191252B4/cs unknown
- 1972-11-15 FR FR7240521A patent/FR2160483B2/fr not_active Expired
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP1907396B1 (fr) | Procede de preparation de la 4 -amino-4'-demethyl-4-desoxypodophyllotoxine | |
| FR2475039A1 (fr) | Amide a, b insature n-substitue | |
| FI59398C (fi) | Foerfarande foer framstaellning av penicillamin och dess homologer | |
| Ohashi et al. | A new method for 5-(4-hydroxyphenyl) hydantoin synthesis | |
| US4452852A (en) | Process for preparing polyfluorinated alcohols | |
| FR2369211A1 (fr) | Procede de preparation d'un acide phosphorique de purete elevee | |
| US4886908A (en) | Method of preparing (R)-4-amino-3-hydroxybutyric acid | |
| FI59399B (fi) | Foerfarande foer framstaellning av penicillamin och dess homologer | |
| US2485225A (en) | Synthesis of hexadiene dinitrile and product | |
| US4845299A (en) | Method for the preparation of bis(hydroxyphenyl) sulfides | |
| EP0093511A1 (en) | Method for producing and optically active 2,2-dimethylcyclopropanecarboxylic acid | |
| US4045479A (en) | Process of preparing penicillamine | |
| CN112969462A (zh) | 乳清酸衍生物的制造方法 | |
| US3948984A (en) | Process of making penicillamine | |
| RU98122366A (ru) | Усовершенствованный способ лактонизации при получении статинов | |
| FR2648134A1 (fr) | Procede pour la fabrication du chlorure de trifluoromethanesulfenyle | |
| US3375252A (en) | Process for the production of 2-methyl-1, 4-diaza-bicyclo-(2, 2, 2)-octane | |
| EP0053400B1 (en) | Process for preparing malononitrile | |
| KR920000953B1 (ko) | 광학활성 3, 4-디히드록시 부티르산 유도체의 제조방법 | |
| US4060548A (en) | Process of making penicillamine | |
| JPS6053021B2 (ja) | ヒダントインの製造法 | |
| IE43243B1 (en) | Prearation of d, l-pantolactone | |
| SU1680692A1 (ru) | Способ получени N-(2,3,3-триметилнорборн-2-ил)монохлорацетамида | |
| RU1631954C (ru) | Способ получения n-ациламинокислот или их солей | |
| SU574438A1 (ru) | П-метакрилилфенил- -нафтиламин в качестве стабилизатора карбоцепных каучуков |