JPH0134218B2 - - Google Patents
Info
- Publication number
- JPH0134218B2 JPH0134218B2 JP7813481A JP7813481A JPH0134218B2 JP H0134218 B2 JPH0134218 B2 JP H0134218B2 JP 7813481 A JP7813481 A JP 7813481A JP 7813481 A JP7813481 A JP 7813481A JP H0134218 B2 JPH0134218 B2 JP H0134218B2
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- carboxylic acid
- exchange resin
- ion exchange
- aziridine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- -1 3-substituted aziridine-2-carboxylic acid Chemical class 0.000 claims description 26
- 230000002378 acidificating effect Effects 0.000 claims description 15
- 239000003729 cation exchange resin Substances 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 238000000034 method Methods 0.000 description 23
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 17
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 17
- 239000004473 Threonine Substances 0.000 description 17
- 239000003456 ion exchange resin Substances 0.000 description 17
- 229920003303 ion-exchange polymer Polymers 0.000 description 17
- 239000007864 aqueous solution Substances 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000002994 raw material Substances 0.000 description 13
- 239000012153 distilled water Substances 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 10
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 9
- 235000011114 ammonium hydroxide Nutrition 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- CXIYBDIJKQJUMN-QMMMGPOBSA-N (2s)-2-anilino-3-hydroxypropanoic acid Chemical compound OC[C@@H](C(O)=O)NC1=CC=CC=C1 CXIYBDIJKQJUMN-QMMMGPOBSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 238000005342 ion exchange Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- LDRFQSZFVGJGGP-GSVOUGTGSA-N 3-hydroxy-L-valine Chemical compound CC(C)(O)[C@H](N)C(O)=O LDRFQSZFVGJGGP-GSVOUGTGSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YDMOQLWVHXRFNI-LURJTMIESA-N (2s)-3-hydroxy-2-(pyridin-2-ylamino)propanoic acid Chemical compound OC[C@@H](C(O)=O)NC1=CC=CC=N1 YDMOQLWVHXRFNI-LURJTMIESA-N 0.000 description 2
- LQNRQHXPYZSWHH-UHFFFAOYSA-N 3,3-dimethylaziridine-2-carboxylic acid Chemical compound CC1(C)NC1C(O)=O LQNRQHXPYZSWHH-UHFFFAOYSA-N 0.000 description 2
- GMYKYCKUEYTTFJ-UHFFFAOYSA-N 3-methylaziridine-2-carbonitrile Chemical compound CC1NC1C#N GMYKYCKUEYTTFJ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 2
- WBGBOXYJYPVLQJ-UHFFFAOYSA-N aziridine-2-carboxylic acid Chemical class OC(=O)C1CN1 WBGBOXYJYPVLQJ-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229940023913 cation exchange resins Drugs 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- BKCZTUQBOINMEQ-UHFFFAOYSA-N propan-2-yl 3-methylaziridine-2-carboxylate Chemical compound CC(C)OC(=O)C1NC1C BKCZTUQBOINMEQ-UHFFFAOYSA-N 0.000 description 2
- IPVXDACNYLWMMK-UHFFFAOYSA-N propan-2-yl 3-phenylaziridine-2-carboxylate Chemical compound CC(C)OC(=O)C1NC1C1=CC=CC=C1 IPVXDACNYLWMMK-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- LYBVTBCJUPMLBJ-HNNXBMFYSA-N (2s)-2-(n-benzylanilino)-3-hydroxypropanoic acid Chemical compound C=1C=CC=CC=1N([C@@H](CO)C(O)=O)CC1=CC=CC=C1 LYBVTBCJUPMLBJ-HNNXBMFYSA-N 0.000 description 1
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- QOISFPILRGBKKL-UHFFFAOYSA-N 3-methylaziridine-2-carboxylic acid Chemical compound CC1NC1C(O)=O QOISFPILRGBKKL-UHFFFAOYSA-N 0.000 description 1
- GPBCRRMRLBDOKI-UHFFFAOYSA-N 3-phenylaziridine-2-carboxamide Chemical compound NC(=O)C1NC1C1=CC=CC=C1 GPBCRRMRLBDOKI-UHFFFAOYSA-N 0.000 description 1
- DUZMKNIYALAIRZ-UHFFFAOYSA-N 5-ethoxy-5h-benzo[7]annulene Chemical compound CCOC1C=CC=CC2=CC=CC=C12 DUZMKNIYALAIRZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical group O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003674 animal food additive Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 235000020776 essential amino acid Nutrition 0.000 description 1
- 239000003797 essential amino acid Substances 0.000 description 1
- CWCDZAMGWWARQB-UHFFFAOYSA-N ethyl 3-methylaziridine-2-carboxylate Chemical compound CCOC(=O)C1NC1C CWCDZAMGWWARQB-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 description 1
- 230000033444 hydroxylation Effects 0.000 description 1
- 238000005805 hydroxylation reaction Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- LDRYRACKTAWHCZ-UHFFFAOYSA-N methyl 3-methylaziridine-2-carboxylate Chemical compound COC(=O)C1NC1C LDRYRACKTAWHCZ-UHFFFAOYSA-N 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- UZSOCTFIMNSUAG-UHFFFAOYSA-N propan-2-yl 3-pyridin-2-ylaziridine-2-carboxylate Chemical compound CC(C)OC(=O)C1NC1C1=CC=CC=N1 UZSOCTFIMNSUAG-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7813481A JPS57193432A (en) | 1981-05-25 | 1981-05-25 | Production of beta-hydroxyaminoacid |
| AU84520/82A AU550973B2 (en) | 1981-05-19 | 1982-03-19 | Process for preparing b-hydroxy amino acid |
| IT21337/82A IT1151414B (it) | 1981-05-19 | 1982-05-18 | Processo per la produzione di beta-idrossiaminoacidi |
| MX192763A MX155815A (es) | 1981-05-19 | 1982-05-19 | Procedimiento para preparar beta-hidroxiamino-acido |
| PCT/JP1982/000182 WO1982004044A1 (fr) | 1981-05-19 | 1982-05-19 | Procede de preparation d'un acide amine (beta)-hydroxy |
| DE8282901531T DE3268091D1 (en) | 1981-05-19 | 1982-05-19 | Process for preparing beta-hydroxy amino acid |
| CA000403290A CA1185979A (fr) | 1981-05-19 | 1982-05-19 | PROCEDE D'OBTENTION D'ACIDES .beta.-HYDROXYAMINO |
| EP82901531A EP0079390B1 (fr) | 1981-05-19 | 1982-05-19 | Procede de preparation d'un acide amine beta-hydroxy |
| KR8202182A KR860001885B1 (ko) | 1981-05-19 | 1982-05-19 | β-히드록시 아미노산의 제조법 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7813481A JPS57193432A (en) | 1981-05-25 | 1981-05-25 | Production of beta-hydroxyaminoacid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57193432A JPS57193432A (en) | 1982-11-27 |
| JPH0134218B2 true JPH0134218B2 (fr) | 1989-07-18 |
Family
ID=13653402
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7813481A Granted JPS57193432A (en) | 1981-05-19 | 1981-05-25 | Production of beta-hydroxyaminoacid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57193432A (fr) |
-
1981
- 1981-05-25 JP JP7813481A patent/JPS57193432A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57193432A (en) | 1982-11-27 |
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