CS225281B1 - The purification of the d,l-threo-2-acetamide-1-/4-nitrophenyl/-1,3-propandiole - Google Patents
The purification of the d,l-threo-2-acetamide-1-/4-nitrophenyl/-1,3-propandiole Download PDFInfo
- Publication number
- CS225281B1 CS225281B1 CS297382A CS297382A CS225281B1 CS 225281 B1 CS225281 B1 CS 225281B1 CS 297382 A CS297382 A CS 297382A CS 297382 A CS297382 A CS 297382A CS 225281 B1 CS225281 B1 CS 225281B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- nitrophenyl
- threo
- purification
- propandiole
- acetamide
- Prior art date
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- 238000000746 purification Methods 0.000 title claims 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 title 1
- 238000000034 method Methods 0.000 claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000012535 impurity Substances 0.000 claims description 3
- 150000002500 ions Chemical class 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 238000010923 batch production Methods 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 238000010924 continuous production Methods 0.000 claims 1
- PIVQDUYOEIAFDM-UHFFFAOYSA-N n-[1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide Chemical compound CC(=O)NC(CO)C(O)C1=CC=C([N+]([O-])=O)C=C1 PIVQDUYOEIAFDM-UHFFFAOYSA-N 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 150000002009 diols Chemical class 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 239000003957 anion exchange resin Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- -1 aluminum compound Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 description 1
- 229960005091 chloramphenicol Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Jedním ze stupňů výroby antibiotika chloramfenikolu je Meerweinova, Ponndorfova a Verleyova redukce D,L-2-acetoamido-3-hydroxy-l-(4-nitrofenyl)-l-propanonu na D,L-threo-2-acetamido-l-(4-nitrofenol)-l,3-propandiol ( I ). Redukce se provádí v bezvodém 2-propanolu účinkem směsí chloro-diisopropoxy a triisopropoxyalánu, přičemž vzniklý aceton se kontinuálně oddestilovávé. Podle známého postupu se diol I izoluje tak, že se na reakční směs po redukci působí vodným roztokem 2-propanolu, čímž se vyloučí sraženina sloučeniny diolu I a hliníku. Po odstranění části 2-propanolu se sloučenina diolu I a hliníku rozloží vodou a diol I přejde do roztoku, kde účinkem bází dojde k vyloučení balastů. Nevýhodou tohoto postupu je to, že použité báze znečišťují produkt, tj. diol I. Tyto nevýhody odstraňuje postup podle předkládaného vynálezu.One step in the production of the antibiotic chloramphenicol is Meerwein, Ponndorf and Verley reduction of D, L-2-acetoamido-3-hydroxy-1- (4-nitrophenyl) -1-propanone to D, L-threo-2-acetamido-1 - ( 4-nitrophenol) -1,3-propanediol (I). The reduction is carried out in anhydrous 2-propanol by the action of mixtures of chloro-diisopropoxy and triisopropoxyalan, whereby the acetone formed is continuously distilled off. According to the known procedure, the diol I is isolated by treating the reaction mixture with an aqueous solution of 2-propanol after reduction, thereby precipitating a diol I compound and an aluminum precipitate. After removal of a portion of the 2-propanol, the diol I and aluminum compound are decomposed with water and the diol I goes into solution, where the ballasts are separated by the action of bases. A disadvantage of this process is that the bases used contaminate the product, i.e. diol I. These disadvantages are overcome by the process of the present invention.
Podle tohoto vynálezu se balastní látky odstraňuji účinkem anexů, přičemž separaci balastů je možné provádět jak v potočných tak vsádkových soustavách. Takto přečištěný produkt dosahuje čistoty 97 až 99,8 %. Vynález a jeho účinky jsou blíže osvětleny na následujícím příkladu provedení.According to the present invention, the ballast materials are removed by means of anion exchange resins, wherein the ballast separation can be carried out in both stream and batch systems. The product thus purified achieves a purity of 97-99.8%. The invention and its effects are illustrated in more detail in the following exemplary embodiment.
225 281225 281
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PříkladExample
Vodný roztok produktů redukce, které byly připraveny dříve popsaným způsobem, o objemu 500 ml, zbavený 2-propanolu, obsahující 7,65 g diolu I a 4,5 g balastních látek byl nanesen na kolonu o průměru 3,6 . 10“2m obsahující 0,3 . 10”3nP silně bazického iontoměniče v OH- cyklu. Roztok protékal kolonou fiktivní rychlostí 4,46 . 10^m.s’1, při teplotě 20 °C. Po zpracování roztoku byla kolona promyta 2 500 ml směsi složené z 1 250 ml methanolu a 750 ml vody a 500 ml konc. vodného roztoku hydroxidu amonného. Eluát byl spojen s roztokem a odpařen, čímž bylo získáno 7,3 g diolu I (95 %). Takto upravený produkt obsahoval méně než 0,5 % nečistot.An aqueous solution of 2-propanol-free reduction products prepared as described above, containing 7.65 g of diol I and 4.5 g of ballasts, was loaded onto a 3.6 mm column. 10 " 2 m containing 0.3. 10 3 3 nP of strongly basic ion exchanger in OH - cycle. The solution flowed through the column at a fictitious rate of 4.46. 10 .mu.m -1 , at 20 ° C. After working up the solution, the column was washed with 2500 ml of a mixture consisting of 1250 ml methanol and 750 ml water and 500 ml conc. aqueous ammonium hydroxide solution. The eluate was combined with the solution and evaporated to give 7.3 g of diol I (95%). The product thus treated contained less than 0.5% impurities.
Diol I a nečistoty obsažené ve výchozím materiálu byly stanoveny pomocí vysokotlaké kapalinové chromátografie.Diol I and impurities contained in the starting material were determined by high pressure liquid chromatography.
Kolona byla promyta vodně alkoholovým roztokem (IQ obj.) 105fe kyseliny chlorovodíkové. Bylo použito 1 000 ml dříve specifikovaného roztoku. Po promytí do neutrality byl anex převeden zpět do OH“ cyklu 0,1 M vodným roztokem hydroxidu sodného.The column was washed with an aqueous alcoholic solution (10 vol.) Of 10 5fe hydrochloric acid. 1000 ml of the previously specified solution was used. After washing to neutrality, the anion exchange resin was transferred back to the OH-cycle with a 0.1 M aqueous sodium hydroxide solution.
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS297382A CS225281B1 (en) | 1982-01-26 | 1982-01-26 | The purification of the d,l-threo-2-acetamide-1-/4-nitrophenyl/-1,3-propandiole |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS297382A CS225281B1 (en) | 1982-01-26 | 1982-01-26 | The purification of the d,l-threo-2-acetamide-1-/4-nitrophenyl/-1,3-propandiole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS225281B1 true CS225281B1 (en) | 1984-02-13 |
Family
ID=5368476
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS297382A CS225281B1 (en) | 1982-01-26 | 1982-01-26 | The purification of the d,l-threo-2-acetamide-1-/4-nitrophenyl/-1,3-propandiole |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS225281B1 (en) |
-
1982
- 1982-01-26 CS CS297382A patent/CS225281B1/en unknown
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