CS199501B2 - Process for preparing 2-deutero-3-fluor-dl-alanine - Google Patents
Process for preparing 2-deutero-3-fluor-dl-alanine Download PDFInfo
- Publication number
- CS199501B2 CS199501B2 CS757421A CS742175A CS199501B2 CS 199501 B2 CS199501 B2 CS 199501B2 CS 757421 A CS757421 A CS 757421A CS 742175 A CS742175 A CS 742175A CS 199501 B2 CS199501 B2 CS 199501B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- hydrate
- borodeuteride
- acid
- salt
- alkali metal
- Prior art date
Links
- UYTSRQMXRROFPU-VMNATFBRSA-N 2-amino-2-deuterio-3-fluoropropanoic acid Chemical compound FCC(N)([2H])C(O)=O UYTSRQMXRROFPU-VMNATFBRSA-N 0.000 title abstract description 7
- 238000004519 manufacturing process Methods 0.000 title 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 44
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000000203 mixture Substances 0.000 claims abstract description 17
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 15
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 14
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims abstract description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims abstract description 8
- 239000002253 acid Substances 0.000 claims abstract description 8
- OSYXANRNDYBMOU-UHFFFAOYSA-N 3-fluoro-2-iminopropanoic acid Chemical compound OC(=O)C(=N)CF OSYXANRNDYBMOU-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000012354 sodium borodeuteride Substances 0.000 claims abstract description 5
- 239000003054 catalyst Substances 0.000 claims abstract description 4
- 239000011780 sodium chloride Substances 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 15
- -1 alkaline earth metal salt Chemical class 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- CXABZTLXNODUTD-UHFFFAOYSA-N 3-fluoropyruvic acid Chemical compound OC(=O)C(=O)CF CXABZTLXNODUTD-UHFFFAOYSA-N 0.000 claims description 7
- 239000000908 ammonium hydroxide Substances 0.000 claims description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- OSJTUAARHMVOHR-UHFFFAOYSA-M lithium;3-fluoro-2-oxopropanoate Chemical compound [Li+].[O-]C(=O)C(=O)CF OSJTUAARHMVOHR-UHFFFAOYSA-M 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 8
- 239000003638 chemical reducing agent Substances 0.000 abstract description 6
- 238000006268 reductive amination reaction Methods 0.000 abstract description 6
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract description 5
- 230000002378 acidificating effect Effects 0.000 abstract description 5
- 229910052744 lithium Inorganic materials 0.000 abstract description 5
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 abstract description 4
- 238000001816 cooling Methods 0.000 abstract description 4
- 239000003610 charcoal Substances 0.000 abstract description 3
- 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 abstract 1
- 239000003729 cation exchange resin Substances 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 24
- 238000006722 reduction reaction Methods 0.000 description 20
- 150000002466 imines Chemical class 0.000 description 18
- 235000011114 ammonium hydroxide Nutrition 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 238000011067 equilibration Methods 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
- RRYOTPCFMILDDZ-UHFFFAOYSA-M lithium;3-fluoro-2-oxopropanoate;hydrate Chemical compound [Li+].O.[O-]C(=O)C(=O)CF RRYOTPCFMILDDZ-UHFFFAOYSA-M 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 230000002829 reductive effect Effects 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- UYIAUFVPRSSBGY-VMNATFBRSA-N 2-deuterio-3-fluoro-2-hydroxypropanoic acid Chemical compound FCC(O)([2H])C(O)=O UYIAUFVPRSSBGY-VMNATFBRSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- UYTSRQMXRROFPU-LIIDHCAMSA-N (2s)-2-amino-2-deuterio-3-fluoropropanoic acid Chemical compound FC[C@](N)([2H])C(O)=O UYTSRQMXRROFPU-LIIDHCAMSA-N 0.000 description 1
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 1
- AQVIWPOYCZKUAH-UHFFFAOYSA-N 2-amino-3-fluoro-2-hydroxypropanoic acid Chemical compound FCC(O)(N)C(O)=O AQVIWPOYCZKUAH-UHFFFAOYSA-N 0.000 description 1
- RLRSEGOXKMMOLT-UHFFFAOYSA-N 3-fluoro-2,2-dihydroxypropanoic acid Chemical compound OC(=O)C(O)(O)CF RLRSEGOXKMMOLT-UHFFFAOYSA-N 0.000 description 1
- NNUPCDRECHRJDC-UHFFFAOYSA-N 3-fluoro-2-iminopropanoic acid;hydrate Chemical compound O.OC(=O)C(=N)CF NNUPCDRECHRJDC-UHFFFAOYSA-N 0.000 description 1
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- MXZIBHAGKDUZKQ-UHFFFAOYSA-N OC(C(=O)O)(CF)O.C(C(=O)C)(=O)O Chemical compound OC(C(=O)O)(CF)O.C(C(=O)C)(=O)O MXZIBHAGKDUZKQ-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- LYZMTNFFOABCIM-UHFFFAOYSA-L calcium;3-fluoro-2-oxopropanoate Chemical compound [Ca+2].[O-]C(=O)C(=O)CF.[O-]C(=O)C(=O)CF LYZMTNFFOABCIM-UHFFFAOYSA-L 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 description 1
- 229960002050 hydrofluoric acid Drugs 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- YEXRRCHQJDSEJI-UHFFFAOYSA-M sodium;3-fluoro-2-oxopropanoate Chemical compound [Na+].[O-]C(=O)C(=O)CF YEXRRCHQJDSEJI-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- 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
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
- C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Oncology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/522,185 US3972921A (en) | 1974-11-08 | 1974-11-08 | Synthesis of racemic 2-deutero-3-fluoro-alanine and its salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS199501B2 true CS199501B2 (en) | 1980-07-31 |
Family
ID=24079796
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS757421A CS199501B2 (en) | 1974-11-08 | 1975-11-04 | Process for preparing 2-deutero-3-fluor-dl-alanine |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US3972921A (en, 2012) |
| JP (1) | JPS5926614B2 (en, 2012) |
| AR (1) | AR208722A1 (en, 2012) |
| AT (1) | AT344136B (en, 2012) |
| BE (1) | BE835358A (en, 2012) |
| CA (1) | CA1053697A (en, 2012) |
| CH (1) | CH622772A5 (en, 2012) |
| CS (1) | CS199501B2 (en, 2012) |
| DD (1) | DD125839A5 (en, 2012) |
| DE (1) | DE2550121C2 (en, 2012) |
| DK (1) | DK474375A (en, 2012) |
| ES (1) | ES442154A1 (en, 2012) |
| FI (1) | FI752919A7 (en, 2012) |
| FR (1) | FR2290418A1 (en, 2012) |
| GB (1) | GB1480886A (en, 2012) |
| HU (1) | HU172273B (en, 2012) |
| IE (1) | IE42060B1 (en, 2012) |
| IT (1) | IT1048054B (en, 2012) |
| LU (1) | LU73734A1 (en, 2012) |
| NL (1) | NL7512383A (en, 2012) |
| NO (1) | NO147671C (en, 2012) |
| PL (1) | PL102608B1 (en, 2012) |
| SE (1) | SE7511734L (en, 2012) |
| SU (1) | SU626689A3 (en, 2012) |
| YU (1) | YU39750B (en, 2012) |
| ZA (1) | ZA757012B (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4028405A (en) * | 1974-10-15 | 1977-06-07 | Merck & Co., Inc. | Fluorinated amino acids |
| US4049708A (en) * | 1976-03-04 | 1977-09-20 | Merck & Co., Inc. | Fluorodesulfurization of alkyl mercaptans or alkyl dithianes |
| NZ194348A (en) * | 1979-07-26 | 1982-09-14 | Merrell Toraude & Co | Fluorinated methyl-beta-alanine derivatives and pharmaceutical compositions |
| JPS56113733A (en) * | 1979-12-29 | 1981-09-07 | Daikin Ind Ltd | 3-substituted-3-fluoropyruvic acid, its ester, salt and preparation thereof |
| US4582931A (en) * | 1984-12-24 | 1986-04-15 | Merck & Co., Inc. | Preparation of 2-Deutero-D-serine |
| US5254730A (en) * | 1992-01-14 | 1993-10-19 | Kilgore James L | Production of amino acids and amino acid derivatives bearing isotopic hydrogen labels |
| FR2707309B1 (fr) * | 1993-07-09 | 1995-08-11 | Trefileurope France Sa | Câble de levage. |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2610212A (en) * | 1950-04-24 | 1952-09-09 | Gen Mills Inc | Synthesis of amino acids |
| US2839547A (en) * | 1955-07-30 | 1958-06-17 | Inventa Ag | Process for the production of aminocarboxylic acids |
| JPS4936389B1 (en, 2012) * | 1969-03-03 | 1974-09-30 | ||
| US3585361A (en) * | 1969-06-18 | 1971-06-15 | Nordson Corp | Supply system for heating and dispensing molten thermoplastic material |
| JPS4841007B1 (en, 2012) * | 1970-10-22 | 1973-12-04 | ||
| JPS5225415B2 (en, 2012) * | 1972-01-17 | 1977-07-07 | ||
| JPS4935435A (en, 2012) * | 1972-08-09 | 1974-04-02 |
-
1974
- 1974-11-08 US US05/522,185 patent/US3972921A/en not_active Expired - Lifetime
-
1975
- 1975-10-20 SE SE7511734A patent/SE7511734L/xx unknown
- 1975-10-20 FI FI752919A patent/FI752919A7/fi not_active Application Discontinuation
- 1975-10-22 NL NL7512383A patent/NL7512383A/xx not_active Application Discontinuation
- 1975-10-22 DK DK474375A patent/DK474375A/da not_active Application Discontinuation
- 1975-10-23 NO NO753561A patent/NO147671C/no unknown
- 1975-10-27 YU YU2722/75A patent/YU39750B/xx unknown
- 1975-10-27 CA CA238,618A patent/CA1053697A/en not_active Expired
- 1975-10-27 GB GB44182/75A patent/GB1480886A/en not_active Expired
- 1975-10-28 ES ES442154A patent/ES442154A1/es not_active Expired
- 1975-10-28 AR AR260981A patent/AR208722A1/es active
- 1975-10-31 IT IT52036/75A patent/IT1048054B/it active
- 1975-10-31 SU SU752185056A patent/SU626689A3/ru active
- 1975-10-31 HU HU75ME00001914A patent/HU172273B/hu unknown
- 1975-11-04 CS CS757421A patent/CS199501B2/cs unknown
- 1975-11-04 AT AT838775A patent/AT344136B/de not_active IP Right Cessation
- 1975-11-05 FR FR7533779A patent/FR2290418A1/fr active Granted
- 1975-11-05 IE IE2407/75A patent/IE42060B1/en unknown
- 1975-11-05 DD DD189260A patent/DD125839A5/xx unknown
- 1975-11-06 PL PL1975184521A patent/PL102608B1/pl unknown
- 1975-11-06 LU LU73734A patent/LU73734A1/xx unknown
- 1975-11-06 CH CH1435875A patent/CH622772A5/de not_active IP Right Cessation
- 1975-11-07 DE DE2550121A patent/DE2550121C2/de not_active Expired
- 1975-11-07 JP JP50133150A patent/JPS5926614B2/ja not_active Expired
- 1975-11-07 BE BE161682A patent/BE835358A/xx not_active IP Right Cessation
- 1975-11-07 ZA ZA757012A patent/ZA757012B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL7512383A (nl) | 1976-05-11 |
| CH622772A5 (en, 2012) | 1981-04-30 |
| IE42060L (en) | 1976-05-08 |
| AT344136B (de) | 1978-07-10 |
| FI752919A7 (en, 2012) | 1976-05-09 |
| FR2290418B1 (en, 2012) | 1979-01-05 |
| DD125839A5 (en, 2012) | 1977-05-25 |
| YU39750B (en) | 1985-04-30 |
| NO753561L (en, 2012) | 1976-05-11 |
| SU626689A3 (ru) | 1978-09-30 |
| NO147671B (no) | 1983-02-14 |
| DK474375A (da) | 1976-05-09 |
| BE835358A (fr) | 1976-05-07 |
| GB1480886A (en) | 1977-07-27 |
| CA1053697A (en) | 1979-05-01 |
| IT1048054B (it) | 1980-11-20 |
| FR2290418A1 (fr) | 1976-06-04 |
| ATA838775A (de) | 1977-11-15 |
| JPS5170722A (en) | 1976-06-18 |
| DE2550121A1 (de) | 1976-05-20 |
| LU73734A1 (en, 2012) | 1976-09-06 |
| US3972921A (en) | 1976-08-03 |
| PL102608B1 (pl) | 1979-04-30 |
| JPS5926614B2 (ja) | 1984-06-29 |
| AR208722A1 (es) | 1977-02-28 |
| IE42060B1 (en) | 1980-05-21 |
| HU172273B (hu) | 1978-07-28 |
| ES442154A1 (es) | 1977-07-01 |
| ZA757012B (en) | 1977-06-29 |
| NO147671C (no) | 1983-05-25 |
| AU8605675A (en) | 1977-05-05 |
| SE7511734L (sv) | 1976-05-10 |
| DE2550121C2 (de) | 1984-08-16 |
| YU272275A (en) | 1982-02-28 |
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