IE43351L - 2-deutero-3-fluoro-d-alanine - Google Patents
2-deutero-3-fluoro-d-alanineInfo
- Publication number
- IE43351L IE43351L IE760335A IE33576A IE43351L IE 43351 L IE43351 L IE 43351L IE 760335 A IE760335 A IE 760335A IE 33576 A IE33576 A IE 33576A IE 43351 L IE43351 L IE 43351L
- Authority
- IE
- Ireland
- Prior art keywords
- deutero
- fluoro
- alanine
- isomer
- halo
- Prior art date
Links
- 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 title abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 abstract 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 244000052616 bacterial pathogen Species 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000005764 inhibitory process Effects 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 235000010288 sodium nitrite Nutrition 0.000 abstract 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)
Abstract
2-Deutero-3-fluoro-L-alanine is converted into its D-isomer in an asymmetrical manner. In this process, the L-isomer is reacted with sodium nitrite to give the corresponding L-2-deutero-2-halo-3-fluoro-propionic acid in solution in an aqueous hydrohalic acid. This L-2-deutero-2-halo-3-fluoropropionic acid is then reacted either with ammonia or with sodium azide with replacement of the 2-halogen substituent by a 2-azido group and subsequent catalytic hydrogenation to give 2-deutero-3-fluoro-D-alanine. 2-Deutero-3-fluoro-L-alanine can be converted into pharmaceutically acceptable salts. The resulting compound can be used for inhibition of the growth of Gram-positive and Gram-negative pathogenic bacteria.
[GB1488332A]
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 (2)
| Publication Number | Publication Date |
|---|---|
| IE43351L true IE43351L (en) | 1976-08-21 |
| IE43351B1 IE43351B1 (en) | 1981-02-11 |
Family
ID=24205490
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE335/76A IE43351B1 (en) | 1975-02-24 | 1976-02-20 | Processes for asymmetric conversion of 3-fluoro-l-alanine and 2-deutero-3-fluoro-l-alanine to their d-isomers |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS51110513A (en) |
| AR (1) | AR207277A1 (en) |
| AU (1) | AU500536B2 (en) |
| CA (1) | CA1045157A (en) |
| CH (1) | CH620194A5 (en) |
| CS (1) | CS199274B2 (en) |
| DE (1) | DE2607252A1 (en) |
| DK (1) | DK55976A (en) |
| ES (1) | ES445381A1 (en) |
| FI (1) | FI760302A7 (en) |
| FR (1) | FR2301513A1 (en) |
| GB (1) | GB1488332A (en) |
| GR (1) | GR59306B (en) |
| HU (1) | HU173362B (en) |
| IE (1) | IE43351B1 (en) |
| NL (1) | NL7601511A (en) |
| NO (1) | NO760448L (en) |
| PT (1) | PT64805B (en) |
| SE (1) | SE7601423L (en) |
| YU (1) | YU41876A (en) |
| ZA (1) | ZA761045B (en) |
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/en active
- 1976-02-09 FI FI760302A patent/FI760302A7/fi not_active Application Discontinuation
- 1976-02-10 SE SE7601423A patent/SE7601423L/en unknown
- 1976-02-11 DK DK55976*#A patent/DK55976A/en unknown
- 1976-02-12 NO NO760448A patent/NO760448L/no unknown
- 1976-02-13 NL NL7601511A patent/NL7601511A/en not_active Application Discontinuation
- 1976-02-16 PT PT64805A patent/PT64805B/en unknown
- 1976-02-17 GR GR50072A patent/GR59306B/en unknown
- 1976-02-17 CH CH193076A patent/CH620194A5/en not_active IP Right Cessation
- 1976-02-17 AU AU11178/76A patent/AU500536B2/en not_active Expired
- 1976-02-18 CA CA246,060A patent/CA1045157A/en not_active Expired
- 1976-02-19 YU YU00418/76A patent/YU41876A/en unknown
- 1976-02-19 GB GB6655/76A patent/GB1488332A/en not_active Expired
- 1976-02-20 FR FR7604715A patent/FR2301513A1/en active Granted
- 1976-02-20 ES ES445381A patent/ES445381A1/en not_active Expired
- 1976-02-20 IE IE335/76A patent/IE43351B1/en unknown
- 1976-02-23 ZA ZA761045A patent/ZA761045B/en unknown
- 1976-02-23 CS CS761182A patent/CS199274B2/en unknown
- 1976-02-23 DE DE19762607252 patent/DE2607252A1/en not_active Withdrawn
- 1976-02-24 HU HU76ME1954A patent/HU173362B/en unknown
- 1976-02-24 JP JP51018580A patent/JPS51110513A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| PT64805A (en) | 1976-03-01 |
| AU1117876A (en) | 1977-08-25 |
| JPS51110513A (en) | 1976-09-30 |
| GR59306B (en) | 1977-12-12 |
| FI760302A7 (en) | 1976-08-25 |
| ZA761045B (en) | 1977-09-28 |
| NO760448L (en) | 1976-08-25 |
| CA1045157A (en) | 1978-12-26 |
| SE7601423L (en) | 1976-08-25 |
| GB1488332A (en) | 1977-10-12 |
| DK55976A (en) | 1976-08-25 |
| HU173362B (en) | 1979-04-28 |
| AR207277A1 (en) | 1976-09-22 |
| ES445381A1 (en) | 1977-06-01 |
| FR2301513B1 (en) | 1979-02-02 |
| NL7601511A (en) | 1976-08-26 |
| DE2607252A1 (en) | 1976-09-02 |
| AU500536B2 (en) | 1979-05-24 |
| IE43351B1 (en) | 1981-02-11 |
| FR2301513A1 (en) | 1976-09-17 |
| YU41876A (en) | 1982-02-28 |
| CH620194A5 (en) | 1980-11-14 |
| PT64805B (en) | 1978-02-06 |
| CS199274B2 (en) | 1980-07-31 |
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