PL84510B1 - - Google Patents
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- Publication number
- PL84510B1 PL84510B1 PL1973160435A PL16043573A PL84510B1 PL 84510 B1 PL84510 B1 PL 84510B1 PL 1973160435 A PL1973160435 A PL 1973160435A PL 16043573 A PL16043573 A PL 16043573A PL 84510 B1 PL84510 B1 PL 84510B1
- Authority
- PL
- Poland
- Prior art keywords
- fluoro
- alanine
- nitrile
- fluoroacetic
- aldehyde
- Prior art date
Links
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 10
- 150000002825 nitriles Chemical class 0.000 claims description 10
- UYTSRQMXRROFPU-UWTATZPHSA-N (2s)-2-amino-3-fluoropropanoic acid Chemical compound FC[C@@H](N)C(O)=O UYTSRQMXRROFPU-UWTATZPHSA-N 0.000 claims description 9
- -1 D-α-carboxybenzylamino Chemical group 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 5
- 150000002466 imines Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 claims description 4
- RQEUFEKYXDPUSK-SSDOTTSWSA-N (1R)-1-phenylethanamine Chemical compound C[C@@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-SSDOTTSWSA-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
- 239000002253 acid Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 4
- 238000003776 cleavage reaction Methods 0.000 claims 2
- 230000007017 scission Effects 0.000 claims 2
- KULGXYMZHFJBHV-VTLYIQCISA-N Cl.C(=O)(O)[C@@H](C1=CC=CC=C1)N[C@H](CF)C(=O)O Chemical compound Cl.C(=O)(O)[C@@H](C1=CC=CC=C1)N[C@H](CF)C(=O)O KULGXYMZHFJBHV-VTLYIQCISA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- BXUGTBKNXOBNNP-HSHFZTNMSA-N (2s)-2-amino-3-fluoropropanoic acid;hydrochloride Chemical compound Cl.FC[C@@H](N)C(O)=O BXUGTBKNXOBNNP-HSHFZTNMSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Natural products CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 235000011132 calcium sulphate Nutrition 0.000 description 2
- 239000001175 calcium sulphate Substances 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- YYDWYJJLVYDJLV-UHFFFAOYSA-N fluoroacetaldehyde Chemical compound FCC=O YYDWYJJLVYDJLV-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229940095564 anhydrous calcium sulfate Drugs 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001768 cations Chemical class 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
- 238000010438 heat treatment Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000006178 methyl benzyl group Chemical group 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B53/00—Asymmetric syntheses
-
- 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
- C07C227/30—Preparation of optical isomers
- C07C227/32—Preparation of optical isomers by stereospecific synthesis
-
- 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
- C07C229/04—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 being acyclic and saturated
- C07C229/20—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 being acyclic and saturated the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US223340A US3903150A (en) | 1972-02-03 | 1972-02-03 | Process for preparing 3-fluoro-D-alanine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL84510B1 true PL84510B1 (forum.php) | 1976-04-30 |
Family
ID=22836086
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1973160435A PL84510B1 (forum.php) | 1972-02-03 | 1973-01-27 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3903150A (forum.php) |
| JP (1) | JPS4885522A (forum.php) |
| AT (1) | AT326096B (forum.php) |
| CA (1) | CA1001650A (forum.php) |
| CH (1) | CH582648A5 (forum.php) |
| CS (1) | CS178123B2 (forum.php) |
| DD (1) | DD108074A5 (forum.php) |
| ES (1) | ES411142A1 (forum.php) |
| HU (1) | HU169231B (forum.php) |
| NL (1) | NL7300575A (forum.php) |
| PL (1) | PL84510B1 (forum.php) |
| SE (1) | SE402008B (forum.php) |
| SU (1) | SU484682A3 (forum.php) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1111444A (en) * | 1979-06-08 | 1981-10-27 | Kazuo Nakayasu | Process for production of beta-chloroalanine |
| US5319096A (en) * | 1992-04-03 | 1994-06-07 | Hoechst-Roussel Pharmaceuticals Inc. | (1H-indol-1-yl)-2-(amino) acetamides and related (1H-indol-1-yl)-(aminoalkyl)amides, pharmaceutical composition and use |
| US6436344B1 (en) * | 1999-11-02 | 2002-08-20 | American National Red Cross | Method of inactivating pathogens |
-
1972
- 1972-02-03 US US223340A patent/US3903150A/en not_active Expired - Lifetime
-
1973
- 1973-01-15 NL NL7300575A patent/NL7300575A/xx not_active Application Discontinuation
- 1973-01-18 SE SE7300698A patent/SE402008B/xx unknown
- 1973-01-22 CS CS477A patent/CS178123B2/cs unknown
- 1973-01-24 CA CA161,903A patent/CA1001650A/en not_active Expired
- 1973-01-27 PL PL1973160435A patent/PL84510B1/pl unknown
- 1973-01-30 AT AT78973A patent/AT326096B/de not_active IP Right Cessation
- 1973-01-31 ES ES411142A patent/ES411142A1/es not_active Expired
- 1973-02-01 SU SU1878072A patent/SU484682A3/ru active
- 1973-02-01 DD DD168609A patent/DD108074A5/xx unknown
- 1973-02-02 HU HUME1600A patent/HU169231B/hu unknown
- 1973-02-02 JP JP48013022A patent/JPS4885522A/ja active Pending
- 1973-02-02 CH CH148873A patent/CH582648A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CS178123B2 (forum.php) | 1977-08-31 |
| JPS4885522A (forum.php) | 1973-11-13 |
| US3903150A (en) | 1975-09-02 |
| CA1001650A (en) | 1976-12-14 |
| CH582648A5 (forum.php) | 1976-12-15 |
| SU484682A3 (ru) | 1975-09-15 |
| HU169231B (forum.php) | 1976-10-28 |
| NL7300575A (forum.php) | 1973-08-07 |
| ATA78973A (de) | 1975-02-15 |
| ES411142A1 (es) | 1975-12-01 |
| DD108074A5 (forum.php) | 1974-09-05 |
| SE402008B (sv) | 1978-06-12 |
| AT326096B (de) | 1975-11-25 |
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