CA1054158A - Process for resolution of 2-deutero-3-fluoro-dl-alanine salts - Google Patents
Process for resolution of 2-deutero-3-fluoro-dl-alanine saltsInfo
- Publication number
- CA1054158A CA1054158A CA231,941A CA231941A CA1054158A CA 1054158 A CA1054158 A CA 1054158A CA 231941 A CA231941 A CA 231941A CA 1054158 A CA1054158 A CA 1054158A
- Authority
- CA
- Canada
- Prior art keywords
- deutero
- fluoro
- solution
- alanine
- benzene sulfonate
- 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 description 13
- UYTSRQMXRROFPU-VMNATFBRSA-N 2-amino-2-deuterio-3-fluoropropanoic acid Chemical class FCC(N)([2H])C(O)=O UYTSRQMXRROFPU-VMNATFBRSA-N 0.000 title description 5
- XOXBTKOKBQADJP-NGRIDVMYSA-N 2-amino-2-deuterio-3-fluoropropanoic acid;benzenesulfonic acid Chemical compound FCC(N)([2H])C(O)=O.OS(=O)(=O)C1=CC=CC=C1 XOXBTKOKBQADJP-NGRIDVMYSA-N 0.000 claims abstract description 11
- 238000002425 crystallisation Methods 0.000 claims abstract description 11
- 230000008025 crystallization Effects 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims abstract description 10
- 239000012047 saturated solution Substances 0.000 claims abstract description 4
- 238000010924 continuous production Methods 0.000 claims abstract 3
- 239000000243 solution Substances 0.000 claims description 31
- 229940077388 benzenesulfonate Drugs 0.000 claims description 14
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical class CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 12
- 239000012452 mother liquor Substances 0.000 claims description 11
- XOXBTKOKBQADJP-DWXPJDSVSA-N (2s)-2-amino-2-deuterio-3-fluoropropanoic acid;benzenesulfonic acid Chemical compound FC[C@](N)([2H])C(O)=O.OS(=O)(=O)C1=CC=CC=C1 XOXBTKOKBQADJP-DWXPJDSVSA-N 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 239000013078 crystal Substances 0.000 claims description 7
- -1 2-deutero-3-fluoro-D-alanine benzene Chemical compound 0.000 claims description 4
- 230000001131 transforming effect Effects 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims 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 abstract description 8
- 239000003242 anti bacterial agent Substances 0.000 abstract description 3
- 230000003389 potentiating effect Effects 0.000 abstract description 3
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 238000011109 contamination Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 229960003767 alanine Drugs 0.000 description 2
- 244000052616 bacterial pathogen Species 0.000 description 2
- 239000002178 crystalline material Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000005086 pumping Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DHALQLNIDMSKHU-UWTATZPHSA-N (2r)-2-(fluoroamino)propanoic acid Chemical compound FN[C@H](C)C(O)=O DHALQLNIDMSKHU-UWTATZPHSA-N 0.000 description 1
- KOHJIZNVQLKURI-NGRIDVMYSA-N 2-amino-2-deuterio-3-fluoropropanoic acid benzene Chemical compound C1=CC=CC=C1.[2H]C(N)(CF)C(=O)O KOHJIZNVQLKURI-NGRIDVMYSA-N 0.000 description 1
- RTAPYDYQORHWRY-UHFFFAOYSA-N 2-aminopropanoic acid;benzenesulfonic acid Chemical compound CC(N)C(O)=O.OS(=O)(=O)C1=CC=CC=C1 RTAPYDYQORHWRY-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- PLRMZEOAPQMDCQ-NGRIDVMYSA-N C1=C(C=CC2=CC=CC=C12)S(=O)(=O)O.[2H]C(N)(CF)C(=O)O Chemical compound C1=C(C=CC2=CC=CC=C12)S(=O)(=O)O.[2H]C(N)(CF)C(=O)O PLRMZEOAPQMDCQ-NGRIDVMYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 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
- C07C227/30—Preparation of optical isomers
- C07C227/34—Preparation of optical isomers by separation of optical isomers
-
- 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)
- Analytical Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US49335274A | 1974-07-31 | 1974-07-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1054158A true CA1054158A (en) | 1979-05-08 |
Family
ID=23959889
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA231,941A Expired CA1054158A (en) | 1974-07-31 | 1975-07-21 | Process for resolution of 2-deutero-3-fluoro-dl-alanine salts |
Country Status (24)
| Country | Link |
|---|---|
| JP (1) | JPS5139626A (sv) |
| AR (1) | AR207648A1 (sv) |
| AU (1) | AU497991B2 (sv) |
| BE (1) | BE831760A (sv) |
| CA (1) | CA1054158A (sv) |
| CH (1) | CH598194A5 (sv) |
| CS (1) | CS191271B2 (sv) |
| DD (1) | DD119209A5 (sv) |
| DE (1) | DE2534031A1 (sv) |
| DK (1) | DK345875A (sv) |
| ES (1) | ES439857A1 (sv) |
| FI (1) | FI752130A (sv) |
| FR (1) | FR2280366A1 (sv) |
| GB (1) | GB1472396A (sv) |
| HU (1) | HU170472B (sv) |
| IE (1) | IE41498B1 (sv) |
| LU (1) | LU73100A1 (sv) |
| NL (1) | NL7508925A (sv) |
| NO (1) | NO752551L (sv) |
| PL (1) | PL103968B1 (sv) |
| SE (1) | SE7508553L (sv) |
| SU (1) | SU568362A3 (sv) |
| YU (1) | YU190675A (sv) |
| ZA (1) | ZA754918B (sv) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4028405A (en) * | 1974-10-15 | 1977-06-07 | Merck & Co., Inc. | Fluorinated amino acids |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7300576A (sv) * | 1972-02-03 | 1973-08-07 |
-
1975
- 1975-01-01 AR AR259830A patent/AR207648A1/es active
- 1975-07-17 NO NO752751A patent/NO752551L/no unknown
- 1975-07-17 IE IE1592/75A patent/IE41498B1/en unknown
- 1975-07-21 CA CA231,941A patent/CA1054158A/en not_active Expired
- 1975-07-23 AU AU83316/75A patent/AU497991B2/en not_active Expired
- 1975-07-24 CH CH968275A patent/CH598194A5/xx not_active IP Right Cessation
- 1975-07-24 FI FI752130A patent/FI752130A/fi not_active Application Discontinuation
- 1975-07-25 YU YU01906/75A patent/YU190675A/xx unknown
- 1975-07-25 NL NL7508925A patent/NL7508925A/xx not_active Application Discontinuation
- 1975-07-25 BE BE158335A patent/BE831760A/xx not_active IP Right Cessation
- 1975-07-28 GB GB3148875A patent/GB1472396A/en not_active Expired
- 1975-07-28 SE SE7508553A patent/SE7508553L/sv unknown
- 1975-07-29 FR FR7523617A patent/FR2280366A1/fr active Granted
- 1975-07-29 DD DD187544A patent/DD119209A5/xx unknown
- 1975-07-30 CS CS755338A patent/CS191271B2/cs unknown
- 1975-07-30 SU SU7502163062A patent/SU568362A3/ru active
- 1975-07-30 ES ES439857A patent/ES439857A1/es not_active Expired
- 1975-07-30 DK DK345875A patent/DK345875A/da unknown
- 1975-07-30 PL PL1975182389A patent/PL103968B1/pl unknown
- 1975-07-30 ZA ZA754918A patent/ZA754918B/xx unknown
- 1975-07-30 LU LU73100A patent/LU73100A1/xx unknown
- 1975-07-30 DE DE19752534031 patent/DE2534031A1/de active Pending
- 1975-07-31 HU HUME1881A patent/HU170472B/hu unknown
- 1975-07-31 JP JP50092656A patent/JPS5139626A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| NL7508925A (nl) | 1976-02-03 |
| GB1472396A (en) | 1977-05-04 |
| NO752551L (sv) | 1976-02-03 |
| AU497991B2 (en) | 1979-02-01 |
| DK345875A (da) | 1976-02-01 |
| ES439857A1 (es) | 1977-06-16 |
| YU190675A (en) | 1984-02-29 |
| AR207648A1 (es) | 1976-10-22 |
| DE2534031A1 (de) | 1976-02-12 |
| PL103968B1 (pl) | 1979-07-31 |
| SE7508553L (sv) | 1976-02-02 |
| HU170472B (sv) | 1977-06-28 |
| FR2280366B1 (sv) | 1982-07-30 |
| JPS5139626A (en) | 1976-04-02 |
| FI752130A (sv) | 1976-02-01 |
| AU8331675A (en) | 1977-01-27 |
| FR2280366A1 (fr) | 1976-02-27 |
| ZA754918B (en) | 1977-03-30 |
| CS191271B2 (en) | 1979-06-29 |
| SU568362A3 (ru) | 1977-08-05 |
| BE831760A (fr) | 1976-01-26 |
| CH598194A5 (sv) | 1978-04-28 |
| IE41498L (en) | 1976-01-31 |
| LU73100A1 (sv) | 1976-05-31 |
| IE41498B1 (en) | 1980-01-16 |
| DD119209A5 (sv) | 1976-04-12 |
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