IE41927L - Preparation of 3-fluoro-dl-alanine - Google Patents
Preparation of 3-fluoro-dl-alanineInfo
- Publication number
- IE41927L IE41927L IE752405A IE240575A IE41927L IE 41927 L IE41927 L IE 41927L IE 752405 A IE752405 A IE 752405A IE 240575 A IE240575 A IE 240575A IE 41927 L IE41927 L IE 41927L
- Authority
- IE
- Ireland
- Prior art keywords
- fluoro
- alanine
- hydrate
- salt
- fluoropropionate
- Prior art date
Links
- UYTSRQMXRROFPU-UHFFFAOYSA-N 2-azaniumyl-3-fluoropropanoate Chemical compound FCC(N)C(O)=O UYTSRQMXRROFPU-UHFFFAOYSA-N 0.000 title abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 abstract 2
- 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
- AQVIWPOYCZKUAH-UHFFFAOYSA-N 2-amino-3-fluoro-2-hydroxypropanoic acid Chemical compound FCC(O)(N)C(O)=O AQVIWPOYCZKUAH-UHFFFAOYSA-N 0.000 abstract 1
- RLRSEGOXKMMOLT-UHFFFAOYSA-N 3-fluoro-2,2-dihydroxypropanoic acid Chemical compound OC(=O)C(O)(O)CF RLRSEGOXKMMOLT-UHFFFAOYSA-N 0.000 abstract 1
- OSYXANRNDYBMOU-UHFFFAOYSA-N 3-fluoro-2-iminopropanoic acid Chemical compound OC(=O)C(=N)CF OSYXANRNDYBMOU-UHFFFAOYSA-N 0.000 abstract 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000003729 cation exchange resin Substances 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 238000010828 elution Methods 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 238000006268 reductive amination reaction Methods 0.000 abstract 1
- 230000002829 reductive effect Effects 0.000 abstract 1
- 239000011780 sodium chloride Substances 0.000 abstract 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
-
- 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
- C07C59/21—Saturated compounds having only one carboxyl group and containing keto groups containing halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1480989 Preparing 3 - fluoro- DL - alanine and salts thereof MERCK & CO Inc 27 Oct 1975 [8 Nov 1974] 44183/75 Heading C2C 3 - Fluoro - DL - alanine or a salt thereof is prepared by subjecting a salt of 3-fluoropyruric acid, or hydrate thereof, to reductive amination using aqueous ammonia to form a salt of 2-imino-3-fluoro-propionic acid, or hydrate thereof, and an alkali metal borohydride as reducing agent, optionally in the presence of NaCl or LiCl as catalyst. In examples, lithium fluoropyrurate hydrate is reacted with concentrated aqueous NH 4 OH at c. 37‹ C. to provide a solution containing about 95 parts of 2- hydroxy-2-amino-3-fluoropropionate to about 5 parts of 2,2-dihydroxy-3-fluoropropionate and, after cooling, NaBH 4 is added. The reaction mixture is distilled under reduced pressure to remove ammonia, acidified with HCl, stirred with activated charcoal, filtered, passed through a cation-exchange resin followed by elution with NH 4 OH, and the eluate recrystallized to provide 3-fluoro-DL-alanine.
[GB1480989A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US52218474A | 1974-11-08 | 1974-11-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE41927L true IE41927L (en) | 1976-05-08 |
| IE41927B1 IE41927B1 (en) | 1980-04-23 |
Family
ID=24079793
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2405/75A IE41927B1 (en) | 1974-11-08 | 1975-11-05 | Preparation of 3-fluoro-dl-alanine salts |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS5170721A (en) |
| AT (1) | AT344675B (en) |
| BE (1) | BE835357A (en) |
| DE (1) | DE2550109A1 (en) |
| DK (1) | DK474475A (en) |
| FR (1) | FR2290417A1 (en) |
| GB (1) | GB1480989A (en) |
| IE (1) | IE41927B1 (en) |
| IT (1) | IT1048053B (en) |
| LU (1) | LU73733A1 (en) |
| NL (1) | NL7512382A (en) |
| SE (1) | SE7511733L (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ194348A (en) * | 1979-07-26 | 1982-09-14 | Merrell Toraude & Co | Fluorinated methyl-beta-alanine derivatives and pharmaceutical compositions |
| EP3293167A1 (en) | 2016-09-09 | 2018-03-14 | Université Catholique De Louvain | [18f]-labelled lactate derivative as pet radiotracer |
| CN117586139B (en) * | 2023-10-24 | 2025-10-14 | 天津大学 | L-alanine crystal and preparation method thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7300577A (en) * | 1972-02-03 | 1973-08-07 |
-
1975
- 1975-10-20 SE SE7511733A patent/SE7511733L/en unknown
- 1975-10-22 DK DK474475A patent/DK474475A/en unknown
- 1975-10-22 NL NL7512382A patent/NL7512382A/en not_active Application Discontinuation
- 1975-10-27 GB GB44183/75A patent/GB1480989A/en not_active Expired
- 1975-10-31 IT IT52035/75A patent/IT1048053B/en active
- 1975-11-04 AT AT838675A patent/AT344675B/en active
- 1975-11-05 FR FR7533778A patent/FR2290417A1/en active Granted
- 1975-11-05 IE IE2405/75A patent/IE41927B1/en unknown
- 1975-11-06 LU LU73733A patent/LU73733A1/xx unknown
- 1975-11-07 DE DE19752550109 patent/DE2550109A1/en not_active Withdrawn
- 1975-11-07 BE BE161681A patent/BE835357A/en unknown
- 1975-11-07 JP JP50133149A patent/JPS5170721A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2290417B1 (en) | 1979-01-05 |
| JPS5170721A (en) | 1976-06-18 |
| FR2290417A1 (en) | 1976-06-04 |
| DK474475A (en) | 1976-05-09 |
| NL7512382A (en) | 1976-05-11 |
| IT1048053B (en) | 1980-11-20 |
| ATA838675A (en) | 1977-12-15 |
| LU73733A1 (en) | 1976-09-06 |
| BE835357A (en) | 1976-05-07 |
| DE2550109A1 (en) | 1976-05-13 |
| IE41927B1 (en) | 1980-04-23 |
| SE7511733L (en) | 1976-05-10 |
| GB1480989A (en) | 1977-07-27 |
| AT344675B (en) | 1978-08-10 |
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