CS197967B1 - Process for cleavage of racemic n-acetyl-d,l-phenylalanine - Google Patents
Process for cleavage of racemic n-acetyl-d,l-phenylalanine Download PDFInfo
- Publication number
- CS197967B1 CS197967B1 CS796578A CS796578A CS197967B1 CS 197967 B1 CS197967 B1 CS 197967B1 CS 796578 A CS796578 A CS 796578A CS 796578 A CS796578 A CS 796578A CS 197967 B1 CS197967 B1 CS 197967B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- phenylalanine
- acetyl
- cleavage
- racemic
- optically active
- Prior art date
Links
- CBQJSKKFNMDLON-UHFFFAOYSA-N N-acetylphenylalanine Chemical compound CC(=O)NC(C(O)=O)CC1=CC=CC=C1 CBQJSKKFNMDLON-UHFFFAOYSA-N 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 3
- 238000003776 cleavage reaction Methods 0.000 title description 4
- 230000007017 scission Effects 0.000 title description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 238000002425 crystallisation Methods 0.000 claims description 4
- 230000008025 crystallization Effects 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 230000020477 pH reduction Effects 0.000 claims description 2
- 239000011877 solvent mixture Substances 0.000 claims description 2
- CBQJSKKFNMDLON-JTQLQIEISA-M N-acetyl-L-phenylalaninate Chemical compound CC(=O)N[C@H](C([O-])=O)CC1=CC=CC=C1 CBQJSKKFNMDLON-JTQLQIEISA-M 0.000 claims 1
- CBQJSKKFNMDLON-JTQLQIEISA-N N-acetyl-L-phenylalanine Chemical compound CC(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 CBQJSKKFNMDLON-JTQLQIEISA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000002285 radioactive effect Effects 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical class C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 238000002306 biochemical method Methods 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 238000009835 boiling Methods 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
- 238000007796 conventional method Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229960002989 glutamic acid Drugs 0.000 description 1
- 239000000320 mechanical mixture Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 229960005190 phenylalanine Drugs 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Vynález se týká Štěpení raeeaického N-acetyl-D,L-fenylalaninu, při kterém je možno získat oba antipody v opticky čistém stavu.The invention relates to the cleavage of radioactive N-acetyl-D, L-phenylalanine in which both antipodes can be obtained in optically pure state.
Kromě biochemických metod se ke Štěpení aminokyselin používá klasického způsobu, spočívajícího v převedení vhodného derivátu, jako acylderivátu, esteru a podobně, na sůl s vhodnou chirální komponentou a v rozdělení směsi diastereoizomemích solí krystalizacl. Z novějších technik je možno uvést Štěpeni racemátů očkováním přesyceného roztoku malým množstvím čistého antipodu, která naSlo praktická uplatnění například při výrobě kyseliny L-glutamová.In addition to biochemical methods, the conventional method of resolving amino acids is to convert a suitable derivative such as an acyl derivative, ester and the like into a salt with a suitable chiral component and to separate the mixture of diastereoisomeric salts by crystallization. More recent techniques include resolution of the racemates by seeding a supersaturated solution with a small amount of pure antipode, which has found practical application, for example, in the production of L-glutamic acid.
Jednou z bází, které jo možno použít ke štěpení raeeaického N-acetylfenylalaninu, je L-(*)-threo-l-(p-nitrofenyl)-2-aaino-l,3-propandiol, který odpadá jako nežádoucí produkt při výrobě antibiotika chloramfenikolu (Ceipel H., J. prakt. Chám. £, 104 /1959/).One of the bases that can be used for the cleavage of radioactive N-acetylphenylalanine is L - (*) - threo-1- (p-nitrophenyl) -2-aaino-1,3-propanediol, which falls off as an undesirable product in the production of the antibiotic chloramphenicol (Ceipel H., J. Prakt. Cham. £ 104 (1959)).
Doaud známá «půaoby Štěpení racemickébo fenylalaninu zdokonaluje vynález, spočívající v tom, že ea ze aoli, připravená z N-acetyl-D,L-fenylalaninu a L-(+)-threo-l-(p-nitrofenyl)-2-amino-l,3-propandiolu, okyselením uvolni částečně opticky aktivní N-acetyl-L-fenylalanin, který se rekrystaluje se směsi rozpouštědel, například ze směsi ethanolu a vody v poměru 1:1.The prior art cleavage of racemic or phenylalanine improves the invention in that the aoli prepared from N-acetyl-D, L-phenylalanine and L - (+) - threo-1- (p-nitrophenyl) -2-amino 1,3-propanediol, by acidification liberates the partially optically active N-acetyl-L-phenylalanine, which is recrystallized from a solvent mixture such as ethanol: water 1: 1.
197 967197 967
197 997197 997
Vynález využívá skutečnosti, 2· u racsmétu, existujícího jako konglomerát, například mechanická směs ekvimolekulárních množství obou antipodů» jo možno rekrystaliaací obohacené směsi dosáhnout přednostní kryatalisaca diatého antipodu. Tímto způsobem es podařilo zvýšit optickou Sistotu produktu na 97 %*The invention makes use of the fact that, in the case of a racemate existing as a conglomerate, for example a mechanical mixture of equimolecular amounts of both antipodes, a preferred crystallization of the dilated antipode can be achieved by recrystallization of the enriched mixture. In this way we managed to increase the optical Sistivity of the product to 97%
Vynález je blíže objasněn na uvedeném příkladu.The invention is illustrated by the following example.
Příklad provedeníExemplary embodiment
Do vroucí vody bylo přidáno 10,6 g L-báze a 10,35 g N-aeetyl-D,L-fenylalaninu a směs byla ponechána stát ke krystalizaci. Po odstátí vylouděné soli byl* acetylaminokyselina uvolněna smícháním s 1 N HC1. Po 2 hodinách se vyloudil N-acetyl-L-fenylalanin (4,6 g) o teplotě tání 155 až 165 °C, («O54g “ ♦ 47»*° 1,18, It«)· Rekrystaliaací se směsi ethanol-voda lil ae teplota táni zvýSila na 164 *8 172 °C, ♦ 53,8°, (c 1,58,10.6 g of L-base and 10.35 g of N-acetyl-D, L-phenylalanine were added to boiling water and the mixture was allowed to stand for crystallization. After standing the precipitated salt, the acetylamino acid was liberated by mixing with 1 N HCl. After 2 hours, N-acetyl-L-phenylalanine (4.6 g) precipitated with a melting point of 155-165 ° C, (" 54 g " -water lil and the melting temperature increased to 164 * 8 172 ° C, ♦ 53.8 °, (c 1.58,
EtOH).EtOH).
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS796578A CS197967B1 (en) | 1978-07-18 | 1978-07-18 | Process for cleavage of racemic n-acetyl-d,l-phenylalanine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS796578A CS197967B1 (en) | 1978-07-18 | 1978-07-18 | Process for cleavage of racemic n-acetyl-d,l-phenylalanine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS197967B1 true CS197967B1 (en) | 1980-05-30 |
Family
ID=5429671
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS796578A CS197967B1 (en) | 1978-07-18 | 1978-07-18 | Process for cleavage of racemic n-acetyl-d,l-phenylalanine |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS197967B1 (en) |
-
1978
- 1978-07-18 CS CS796578A patent/CS197967B1/en unknown
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