DE2540735A1 - Verfahren zur herstellung von d- und l-2-(4-hydroxyphenyl)-glycin - Google Patents
Verfahren zur herstellung von d- und l-2-(4-hydroxyphenyl)-glycinInfo
- Publication number
- DE2540735A1 DE2540735A1 DE19752540735 DE2540735A DE2540735A1 DE 2540735 A1 DE2540735 A1 DE 2540735A1 DE 19752540735 DE19752540735 DE 19752540735 DE 2540735 A DE2540735 A DE 2540735A DE 2540735 A1 DE2540735 A1 DE 2540735A1
- Authority
- DE
- Germany
- Prior art keywords
- glycine
- hydroxyphenyl
- mixture
- toluene
- chloroform
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 33
- LJCWONGJFPCTTL-ZETCQYMHSA-N L-4-hydroxyphenylglycine Chemical compound OC(=O)[C@@H](N)C1=CC=C(O)C=C1 LJCWONGJFPCTTL-ZETCQYMHSA-N 0.000 title claims description 27
- LJCWONGJFPCTTL-SSDOTTSWSA-N D-4-hydroxyphenylglycine Chemical compound [O-]C(=O)[C@H]([NH3+])C1=CC=C(O)C=C1 LJCWONGJFPCTTL-SSDOTTSWSA-N 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 102
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 60
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 45
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 44
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 37
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 25
- 239000012453 solvate Substances 0.000 claims description 25
- LJCWONGJFPCTTL-UHFFFAOYSA-N 4-hydroxyphenylglycine Chemical compound OC(=O)C(N)C1=CC=C(O)C=C1 LJCWONGJFPCTTL-UHFFFAOYSA-N 0.000 claims description 24
- 229940035429 isobutyl alcohol Drugs 0.000 claims description 22
- 239000004471 Glycine Substances 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 9
- 239000002244 precipitate Substances 0.000 claims description 6
- 239000012452 mother liquor Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 10
- 238000001914 filtration Methods 0.000 description 9
- 239000013078 crystal Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- -1 (4-hydroxyphenyl) - Chemical class 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004455 differential thermal analysis Methods 0.000 description 3
- XUJHKPSBHDQIOD-UHFFFAOYSA-N (2-bromo-7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl)methanesulfonic acid Chemical class C1CC2(CS(O)(=O)=O)C(=O)C(Br)C1C2(C)C XUJHKPSBHDQIOD-UHFFFAOYSA-N 0.000 description 2
- LPWHDHFZDJPEOV-UHFFFAOYSA-N 4,7,7-trimethylbicyclo[2.2.1]heptane-3-sulfonic acid Chemical compound C1CC2(C)C(S(O)(=O)=O)CC1C2(C)C LPWHDHFZDJPEOV-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 238000001311 chemical methods and process Methods 0.000 description 2
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 229930186147 Cephalosporin Natural products 0.000 description 1
- 235000001258 Cinchona calisaya Nutrition 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JVVXZOOGOGPDRZ-SLFFLAALSA-N [(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine Chemical compound NC[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 JVVXZOOGOGPDRZ-SLFFLAALSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 description 1
- KMPWYEUPVWOPIM-LSOMNZGLSA-N cinchonine Chemical compound C1=CC=C2C([C@@H]([C@H]3N4CC[C@H]([C@H](C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-LSOMNZGLSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B57/00—Separation of optically-active compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP49105805A JPS5132541A (en) | 1974-09-12 | 1974-09-12 | Dll22 * 44 hidorokishifueniru * gurishinnokogakubunkatsuho |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2540735A1 true DE2540735A1 (de) | 1976-03-25 |
Family
ID=14417314
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752540735 Withdrawn DE2540735A1 (de) | 1974-09-12 | 1975-09-12 | Verfahren zur herstellung von d- und l-2-(4-hydroxyphenyl)-glycin |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4016205A (https=) |
| JP (1) | JPS5132541A (https=) |
| BE (1) | BE833265A (https=) |
| DE (1) | DE2540735A1 (https=) |
| FR (1) | FR2284581A1 (https=) |
| GB (1) | GB1514746A (https=) |
| IT (1) | IT1042479B (https=) |
| NL (1) | NL7510769A (https=) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1547206A (en) * | 1976-09-28 | 1979-06-06 | Pfizer Ltd | Pharmaceutical compositions |
| US4185116A (en) * | 1976-09-28 | 1980-01-22 | Pfizer Inc. | L- and DL- Phenylglycines to treat diseases or conditions attributable to reduced carbohydrate metabolism |
| US4179521A (en) * | 1976-09-28 | 1979-12-18 | Pfizer Inc. | L- and DL-Phenylglycines to treat diseases or conditions attributable to reduced carbohydrate metabolism |
| US4179520A (en) * | 1976-09-28 | 1979-12-18 | Pfizer Inc. | L- and DL-Phenylglycines to treat a disease or condition attributable to reduced blood flow |
| US4186210A (en) * | 1976-09-28 | 1980-01-29 | Pfizer Inc. | Method of treatment with glycinamides |
| NL188407C (nl) * | 1977-10-18 | 1992-06-16 | Kessels Gerard | Werkwijze voor de bereiding van d(-)-alfa-fenylglycine. |
| US4151198A (en) * | 1978-06-02 | 1979-04-24 | American Cyanamid Company | Resolution of N-acyl-DL (+)-phenylalanines |
| DE2826952A1 (de) * | 1978-06-20 | 1980-01-10 | Bayer Ag | Enantiomerentrennung von chiralen carbonsaeuren |
| US4415504A (en) * | 1981-09-21 | 1983-11-15 | Tanabe Seiyaku Co., Ltd. | p-Hydroxyphenylglycine.α-phenylethanesulfonate, process for production thereof and utilization thereof in resolution of p-hydroxyphenylglycine |
| JPS59170059A (ja) * | 1983-03-16 | 1984-09-26 | Tanabe Seiyaku Co Ltd | 光学活性α―アミノ酸の製法 |
| JPH0618278B2 (ja) * | 1988-03-07 | 1994-03-09 | サンケン電気株式会社 | シヨツトキバリア半導体装置 |
| KR980009225A (ko) * | 1996-07-31 | 1998-04-30 | 이승웅 | D-(-)-4-히드록시페닐글리신의 제조방법 |
| KR20160022618A (ko) * | 2014-08-20 | 2016-03-02 | 주식회사 아미노로직스 | D-아르기닌의 제조 방법 |
| KR20170029965A (ko) * | 2015-09-08 | 2017-03-16 | 주식회사 아미노로직스 | D-아르기닌의 제조 방법 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3381031A (en) * | 1962-04-18 | 1968-04-30 | Univ Australian | Resolution of racemic amino acids |
| HU165026B (https=) * | 1972-08-11 | 1974-06-28 | ||
| US3832388A (en) * | 1972-09-07 | 1974-08-27 | R Lorenz | Resolution of 2-(p-hydroxy)phenylglycine |
-
1974
- 1974-09-12 JP JP49105805A patent/JPS5132541A/ja active Granted
-
1975
- 1975-09-10 BE BE159908A patent/BE833265A/xx unknown
- 1975-09-10 FR FR7527765A patent/FR2284581A1/fr active Granted
- 1975-09-11 IT IT27149/75A patent/IT1042479B/it active
- 1975-09-12 DE DE19752540735 patent/DE2540735A1/de not_active Withdrawn
- 1975-09-12 US US05/612,660 patent/US4016205A/en not_active Expired - Lifetime
- 1975-09-12 GB GB37662/75A patent/GB1514746A/en not_active Expired
- 1975-09-12 NL NL7510769A patent/NL7510769A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2284581B1 (https=) | 1978-10-20 |
| JPS5132541A (en) | 1976-03-19 |
| BE833265A (fr) | 1976-03-10 |
| IT1042479B (it) | 1980-01-30 |
| US4016205A (en) | 1977-04-05 |
| GB1514746A (en) | 1978-06-21 |
| FR2284581A1 (fr) | 1976-04-09 |
| NL7510769A (nl) | 1976-03-16 |
| JPS5751380B2 (https=) | 1982-11-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |