CA1045157A - Processes for asymmetric conversion of 3-fluoro-l-alanine and 2-deutero-3-fluoro-l-alanine to their d-isomers - Google Patents
Processes for asymmetric conversion of 3-fluoro-l-alanine and 2-deutero-3-fluoro-l-alanine to their d-isomersInfo
- Publication number
- CA1045157A CA1045157A CA246,060A CA246060A CA1045157A CA 1045157 A CA1045157 A CA 1045157A CA 246060 A CA246060 A CA 246060A CA 1045157 A CA1045157 A CA 1045157A
- Authority
- CA
- Canada
- Prior art keywords
- deutero
- fluoro
- alanine
- acid
- isomer
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 title description 9
- UYTSRQMXRROFPU-REOHCLBHSA-N (2r)-2-amino-3-fluoropropanoic acid Chemical compound FC[C@H](N)C(O)=O UYTSRQMXRROFPU-REOHCLBHSA-N 0.000 title 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 16
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000002253 acid Substances 0.000 claims abstract description 10
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims abstract description 10
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 7
- 235000010288 sodium nitrite Nutrition 0.000 claims abstract description 5
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims abstract description 3
- 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 claims description 5
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 3
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229960003767 alanine Drugs 0.000 description 3
- UYTSRQMXRROFPU-UWTATZPHSA-N (2s)-2-amino-3-fluoropropanoic acid Chemical compound FC[C@@H](N)C(O)=O UYTSRQMXRROFPU-UWTATZPHSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- UYTSRQMXRROFPU-VMNATFBRSA-N 2-amino-2-deuterio-3-fluoropropanoic acid Chemical compound FCC(N)([2H])C(O)=O UYTSRQMXRROFPU-VMNATFBRSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- -1 2-deutero-3-fluoro-propionic acid Chemical compound 0.000 description 1
- RPFXMKLCYJSYDE-UHFFFAOYSA-N 3-fluoropropanoic acid Chemical compound OC(=O)CCF RPFXMKLCYJSYDE-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- 241001072332 Monia Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C247/00—Compounds containing azido groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/15—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing halogen
- C07C53/19—Acids containing three or more carbon atoms
- C07C53/21—Acids containing three or more carbon atoms containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/185—Saturated compounds having only one carboxyl group and containing keto groups
- C07C59/19—Pyruvic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/552,474 US3950411A (en) | 1972-02-03 | 1975-02-24 | Processes for asymmetric conversion of 3-fluoro-L-alanine and 2-deutero-3-fluoro-L-alanine to their D-isomers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1045157A true CA1045157A (en) | 1978-12-26 |
Family
ID=24205490
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA246,060A Expired CA1045157A (en) | 1975-02-24 | 1976-02-18 | Processes for asymmetric conversion of 3-fluoro-l-alanine and 2-deutero-3-fluoro-l-alanine to their d-isomers |
Country Status (21)
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3880922A (en) * | 1972-02-03 | 1975-04-29 | Merck & Co Inc | Process for preparing 3-fluoro-D-alanine by asymmetric rearrangement of 2-(azidocarbonyl)-3-fluoro-propionic ester or nitrile |
-
1976
- 1976-01-01 AR AR262279A patent/AR207277A1/es active
- 1976-02-09 FI FI760302A patent/FI760302A7/fi not_active Application Discontinuation
- 1976-02-10 SE SE7601423A patent/SE7601423L/xx unknown
- 1976-02-11 DK DK55976*#A patent/DK55976A/da unknown
- 1976-02-12 NO NO760448A patent/NO760448L/no unknown
- 1976-02-13 NL NL7601511A patent/NL7601511A/xx not_active Application Discontinuation
- 1976-02-16 PT PT64805A patent/PT64805B/pt unknown
- 1976-02-17 AU AU11178/76A patent/AU500536B2/en not_active Expired
- 1976-02-17 GR GR50072A patent/GR59306B/el unknown
- 1976-02-17 CH CH193076A patent/CH620194A5/de not_active IP Right Cessation
- 1976-02-18 CA CA246,060A patent/CA1045157A/en not_active Expired
- 1976-02-19 YU YU00418/76A patent/YU41876A/xx unknown
- 1976-02-19 GB GB6655/76A patent/GB1488332A/en not_active Expired
- 1976-02-20 FR FR7604715A patent/FR2301513A1/fr active Granted
- 1976-02-20 IE IE335/76A patent/IE43351B1/en unknown
- 1976-02-20 ES ES445381A patent/ES445381A1/es not_active Expired
- 1976-02-23 DE DE19762607252 patent/DE2607252A1/de not_active Withdrawn
- 1976-02-23 CS CS761182A patent/CS199274B2/cs unknown
- 1976-02-23 ZA ZA761045A patent/ZA761045B/xx unknown
- 1976-02-24 JP JP51018580A patent/JPS51110513A/ja active Pending
- 1976-02-24 HU HU76ME1954A patent/HU173362B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK55976A (da) | 1976-08-25 |
| FR2301513A1 (fr) | 1976-09-17 |
| AR207277A1 (es) | 1976-09-22 |
| YU41876A (en) | 1982-02-28 |
| FI760302A7 (enrdf_load_stackoverflow) | 1976-08-25 |
| CS199274B2 (en) | 1980-07-31 |
| HU173362B (hu) | 1979-04-28 |
| NO760448L (enrdf_load_stackoverflow) | 1976-08-25 |
| PT64805A (en) | 1976-03-01 |
| AU1117876A (en) | 1977-08-25 |
| SE7601423L (sv) | 1976-08-25 |
| DE2607252A1 (de) | 1976-09-02 |
| ES445381A1 (es) | 1977-06-01 |
| GR59306B (en) | 1977-12-12 |
| CH620194A5 (en) | 1980-11-14 |
| NL7601511A (nl) | 1976-08-26 |
| AU500536B2 (en) | 1979-05-24 |
| IE43351B1 (en) | 1981-02-11 |
| IE43351L (en) | 1976-08-21 |
| ZA761045B (en) | 1977-09-28 |
| GB1488332A (en) | 1977-10-12 |
| JPS51110513A (enrdf_load_stackoverflow) | 1976-09-30 |
| FR2301513B1 (enrdf_load_stackoverflow) | 1979-02-02 |
| PT64805B (en) | 1978-02-06 |
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