DE2305256A1 - Verfahren zur herstellung von 3fluor-d-alanin - Google Patents
Verfahren zur herstellung von 3fluor-d-alaninInfo
- Publication number
- DE2305256A1 DE2305256A1 DE19732305256 DE2305256A DE2305256A1 DE 2305256 A1 DE2305256 A1 DE 2305256A1 DE 19732305256 DE19732305256 DE 19732305256 DE 2305256 A DE2305256 A DE 2305256A DE 2305256 A1 DE2305256 A1 DE 2305256A1
- Authority
- DE
- Germany
- Prior art keywords
- fluoro
- alanine
- acid
- catalyst
- hydrogen
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims description 8
- UYTSRQMXRROFPU-UWTATZPHSA-N (2s)-2-amino-3-fluoropropanoic acid Chemical compound FC[C@@H](N)C(O)=O UYTSRQMXRROFPU-UWTATZPHSA-N 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000003054 catalyst Substances 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- CXABZTLXNODUTD-UHFFFAOYSA-N 3-fluoropyruvic acid Chemical compound OC(=O)C(=O)CF CXABZTLXNODUTD-UHFFFAOYSA-N 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 9
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 238000005984 hydrogenation reaction Methods 0.000 claims description 5
- 150000008574 D-amino acids Chemical class 0.000 claims description 4
- -1 N-substituted 3-fluoro-D-alanine Chemical class 0.000 claims description 4
- 125000006178 methyl benzyl group Chemical group 0.000 claims description 4
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 claims description 4
- ONIBWKKTOPOVIA-SCSAIBSYSA-N D-Proline Chemical compound OC(=O)[C@H]1CCCN1 ONIBWKKTOPOVIA-SCSAIBSYSA-N 0.000 claims description 3
- ZGUNAGUHMKGQNY-SSDOTTSWSA-N D-alpha-phenylglycine Chemical compound OC(=O)[C@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-SSDOTTSWSA-N 0.000 claims description 3
- 102000004674 D-amino-acid oxidase Human genes 0.000 claims description 3
- 108010003989 D-amino-acid oxidase Proteins 0.000 claims description 3
- 229930182820 D-proline Natural products 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 229940107700 pyruvic acid Drugs 0.000 claims description 3
- DHALQLNIDMSKHU-UWTATZPHSA-N (2r)-2-(fluoroamino)propanoic acid Chemical compound FN[C@H](C)C(O)=O DHALQLNIDMSKHU-UWTATZPHSA-N 0.000 claims description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 2
- 108090000790 Enzymes Proteins 0.000 claims description 2
- 102000004190 Enzymes Human genes 0.000 claims description 2
- 229910052805 deuterium Inorganic materials 0.000 claims description 2
- RQEUFEKYXDPUSK-SSDOTTSWSA-N (1R)-1-phenylethanamine Chemical compound C[C@@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-SSDOTTSWSA-N 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- 125000000468 ketone group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 150000004658 ketimines Chemical class 0.000 description 2
- 239000000047 product 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
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- QNAYBMKLOCPYGJ-UWTATZPHSA-N D-alanine Chemical compound C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 1
- QWCKQJZIFLGMSD-GSVOUGTGSA-N D-alpha-aminobutyric acid Chemical compound CC[C@@H](N)C(O)=O QWCKQJZIFLGMSD-GSVOUGTGSA-N 0.000 description 1
- 108030001081 D-amino-acid transaminases Proteins 0.000 description 1
- FFEARJCKVFRZRR-SCSAIBSYSA-N D-methionine Chemical compound CSCC[C@@H](N)C(O)=O FFEARJCKVFRZRR-SCSAIBSYSA-N 0.000 description 1
- 229930182818 D-methionine Natural products 0.000 description 1
- COLNVLDHVKWLRT-MRVPVSSYSA-N D-phenylalanine Chemical compound OC(=O)[C@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-MRVPVSSYSA-N 0.000 description 1
- 229930182832 D-phenylalanine Natural products 0.000 description 1
- 102000006835 Lamins Human genes 0.000 description 1
- 108010047294 Lamins Proteins 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 210000005053 lamin Anatomy 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000011541 reaction mixture 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
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
- 229940048086 sodium pyrophosphate Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22335572A | 1972-02-03 | 1972-02-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2305256A1 true DE2305256A1 (de) | 1973-08-09 |
Family
ID=22836157
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732305256 Ceased DE2305256A1 (de) | 1972-02-03 | 1973-02-02 | Verfahren zur herstellung von 3fluor-d-alanin |
Country Status (17)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE7511733L (sv) * | 1974-11-08 | 1976-05-10 | Merck & Co Inc | Syntes av recemisk 3-fluoro-alanin och salter derav, samt mellanprodukt i denna syntes |
| EP0798289B1 (de) * | 1996-03-29 | 2001-03-07 | F. Hoffmann-La Roche Ag | Alpha-Iminocarbonsäurederivate |
| CN107715870A (zh) * | 2017-10-13 | 2018-02-23 | 西安凯立新材料股份有限公司 | 一种制备l‑氨基丙醇用钌炭催化剂的制备方法及应用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7207606A (enrdf_load_html_response) * | 1971-06-18 | 1972-12-20 |
-
1973
- 1973-01-15 NL NL7300577A patent/NL7300577A/xx not_active Application Discontinuation
- 1973-01-22 CS CS478A patent/CS178418B2/cs unknown
- 1973-01-23 AU AU51369/73A patent/AU467773B2/en not_active Expired
- 1973-01-24 CA CA161,915A patent/CA1001652A/en not_active Expired
- 1973-01-24 AR AR246271A patent/AR200994A1/es active
- 1973-01-30 AT AT79073A patent/AT324294B/de not_active IP Right Cessation
- 1973-01-31 ES ES411143A patent/ES411143A1/es not_active Expired
- 1973-01-31 PL PL1973160498A patent/PL84511B1/pl unknown
- 1973-02-01 GB GB508773A patent/GB1380382A/en not_active Expired
- 1973-02-01 DD DD168612A patent/DD108522A5/xx unknown
- 1973-02-01 DD DD181401*A patent/DD114594A5/xx unknown
- 1973-02-02 HU HUME1599A patent/HU168659B/hu unknown
- 1973-02-02 ZA ZA730777A patent/ZA73777B/xx unknown
- 1973-02-02 DE DE19732305256 patent/DE2305256A1/de not_active Ceased
- 1973-02-02 CH CH148973A patent/CH585694A5/xx not_active IP Right Cessation
- 1973-02-02 FR FR7303666A patent/FR2170180B1/fr not_active Expired
- 1973-02-02 SU SU1878868A patent/SU485592A3/ru active
- 1973-02-02 JP JP48013024A patent/JPS4885524A/ja active Pending
- 1973-10-01 FR FR7335004A patent/FR2197859B1/fr not_active Expired
- 1973-11-05 AR AR250835A patent/AR202539A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| HU168659B (enrdf_load_html_response) | 1976-06-28 |
| PL84511B1 (en) | 1976-04-30 |
| DD114594A5 (enrdf_load_html_response) | 1975-08-12 |
| CS178418B2 (enrdf_load_html_response) | 1977-09-15 |
| FR2197859A1 (enrdf_load_html_response) | 1974-03-29 |
| FR2170180B1 (enrdf_load_html_response) | 1977-04-22 |
| SU485592A3 (ru) | 1975-09-25 |
| GB1380382A (en) | 1975-01-15 |
| AU5136973A (en) | 1974-07-25 |
| CH585694A5 (enrdf_load_html_response) | 1977-03-15 |
| NL7300577A (enrdf_load_html_response) | 1973-08-07 |
| AT324294B (de) | 1975-08-25 |
| FR2197859B1 (enrdf_load_html_response) | 1977-05-27 |
| AR202539A1 (es) | 1975-06-24 |
| AR200994A1 (es) | 1975-02-06 |
| ZA73777B (en) | 1974-10-30 |
| FR2170180A1 (enrdf_load_html_response) | 1973-09-14 |
| ES411143A1 (es) | 1975-12-01 |
| AU467773B2 (en) | 1975-12-11 |
| JPS4885524A (enrdf_load_html_response) | 1973-11-13 |
| DD108522A5 (enrdf_load_html_response) | 1974-09-20 |
| CA1001652A (en) | 1976-12-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8131 | Rejection |