DE2115529A1 - Verfahren zur Gewinnung von L(-)-3,4-Dihydroxyphenylalanin - Google Patents
Verfahren zur Gewinnung von L(-)-3,4-DihydroxyphenylalaninInfo
- Publication number
- DE2115529A1 DE2115529A1 DE19712115529 DE2115529A DE2115529A1 DE 2115529 A1 DE2115529 A1 DE 2115529A1 DE 19712115529 DE19712115529 DE 19712115529 DE 2115529 A DE2115529 A DE 2115529A DE 2115529 A1 DE2115529 A1 DE 2115529A1
- Authority
- DE
- Germany
- Prior art keywords
- crystallization
- isomer
- dihydroxyphenylalanine
- temperature
- solution
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 31
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 title claims description 20
- 238000002360 preparation method Methods 0.000 title description 2
- WTDRDQBEARUVNC-UHFFFAOYSA-N dopa Chemical compound OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims description 39
- 239000000243 solution Substances 0.000 claims description 34
- 238000002425 crystallisation Methods 0.000 claims description 30
- 230000008025 crystallization Effects 0.000 claims description 30
- 239000013078 crystal Substances 0.000 claims description 25
- 239000012452 mother liquor Substances 0.000 claims description 15
- 238000010956 selective crystallization Methods 0.000 claims description 15
- 229920006395 saturated elastomer Polymers 0.000 claims description 10
- 238000000926 separation method Methods 0.000 claims description 10
- 238000001556 precipitation Methods 0.000 claims description 9
- 238000011081 inoculation Methods 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims 1
- 229940114166 dl dopa Drugs 0.000 description 12
- 230000003287 optical effect Effects 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000012047 saturated solution Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 229940024606 amino acid Drugs 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 238000010899 nucleation Methods 0.000 description 2
- 230000006911 nucleation Effects 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- JETBVOLWZWPMKR-UHFFFAOYSA-N (1-carboxy-2-methylpropyl)azanium;chloride Chemical compound Cl.CC(C)C(N)C(O)=O JETBVOLWZWPMKR-UHFFFAOYSA-N 0.000 description 1
- WTDRDQBEARUVNC-ZCFIWIBFSA-N D-DOPA Chemical compound OC(=O)[C@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-ZCFIWIBFSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 1
- 239000004473 Threonine Substances 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000011549 crystallization solution Substances 0.000 description 1
- PXEDJBXQKAGXNJ-QTNFYWBSSA-L disodium L-glutamate Chemical compound [Na+].[Na+].[O-]C(=O)[C@@H](N)CCC([O-])=O PXEDJBXQKAGXNJ-QTNFYWBSSA-L 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000004992 fission Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 235000013923 monosodium glutamate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
- 229940073490 sodium glutamate Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid group Chemical class S(N)(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
- C07C229/34—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 containing six-membered aromatic rings
- C07C229/36—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 containing six-membered aromatic rings with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton
-
- 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
- C07C227/38—Separation; Purification; Stabilisation; Use of additives
- C07C227/40—Separation; Purification
- C07C227/42—Crystallisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712115529 DE2115529A1 (de) | 1971-03-31 | 1971-03-31 | Verfahren zur Gewinnung von L(-)-3,4-Dihydroxyphenylalanin |
| CH443572A CH572898A5 (enExample) | 1971-03-31 | 1972-03-24 | |
| GB1522472A GB1364982A (en) | 1971-03-31 | 1972-03-30 | Phenylalanine derivatives |
| FR7211354A FR2132287B1 (enExample) | 1971-03-31 | 1972-03-30 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712115529 DE2115529A1 (de) | 1971-03-31 | 1971-03-31 | Verfahren zur Gewinnung von L(-)-3,4-Dihydroxyphenylalanin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2115529A1 true DE2115529A1 (de) | 1972-10-05 |
Family
ID=5803330
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712115529 Pending DE2115529A1 (de) | 1971-03-31 | 1971-03-31 | Verfahren zur Gewinnung von L(-)-3,4-Dihydroxyphenylalanin |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH572898A5 (enExample) |
| DE (1) | DE2115529A1 (enExample) |
| FR (1) | FR2132287B1 (enExample) |
| GB (1) | GB1364982A (enExample) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1241405A (en) * | 1969-04-23 | 1971-08-04 | Ajinomoto Kk | Resolution of phenylalanine derivatives |
-
1971
- 1971-03-31 DE DE19712115529 patent/DE2115529A1/de active Pending
-
1972
- 1972-03-24 CH CH443572A patent/CH572898A5/xx not_active IP Right Cessation
- 1972-03-30 FR FR7211354A patent/FR2132287B1/fr not_active Expired
- 1972-03-30 GB GB1522472A patent/GB1364982A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2132287B1 (enExample) | 1975-10-10 |
| FR2132287A1 (enExample) | 1972-11-17 |
| CH572898A5 (enExample) | 1976-02-27 |
| GB1364982A (en) | 1974-08-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |