NO752551L - - Google Patents
Info
- Publication number
- NO752551L NO752551L NO752751A NO752551A NO752551L NO 752551 L NO752551 L NO 752551L NO 752751 A NO752751 A NO 752751A NO 752551 A NO752551 A NO 752551A NO 752551 L NO752551 L NO 752551L
- Authority
- NO
- Norway
- Prior art keywords
- solution
- deutero
- fluoro
- alanine
- isomer
- Prior art date
Links
- 238000000034 method Methods 0.000 claims abstract description 16
- 238000003776 cleavage reaction Methods 0.000 claims abstract description 9
- 230000007017 scission Effects 0.000 claims abstract description 9
- UYTSRQMXRROFPU-VMNATFBRSA-N 2-amino-2-deuterio-3-fluoropropanoic acid Chemical class FCC(N)([2H])C(O)=O UYTSRQMXRROFPU-VMNATFBRSA-N 0.000 claims abstract description 6
- 239000002904 solvent Substances 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 14
- 239000012452 mother liquor Substances 0.000 claims description 13
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 13
- 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 12
- 239000013078 crystal Substances 0.000 claims description 11
- 238000002425 crystallisation Methods 0.000 claims description 11
- 230000008025 crystallization Effects 0.000 claims description 11
- 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 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 238000004090 dissolution Methods 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 238000010924 continuous production Methods 0.000 claims description 3
- DHALQLNIDMSKHU-UWTATZPHSA-N (2r)-2-(fluoroamino)propanoic acid Chemical class FN[C@H](C)C(O)=O DHALQLNIDMSKHU-UWTATZPHSA-N 0.000 claims description 2
- DHALQLNIDMSKHU-UHFFFAOYSA-N 2-(fluoroamino)propanoic acid Chemical class FNC(C)C(O)=O DHALQLNIDMSKHU-UHFFFAOYSA-N 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- 229940077388 benzenesulfonate Drugs 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 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 description 5
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000002178 crystalline material Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000007790 solid phase Substances 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 244000052616 bacterial pathogen Species 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 229950010030 dl-alanine Drugs 0.000 description 2
- 230000002401 inhibitory effect 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
- 239000002002 slurry Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- -1 2-deutero-3-fluoro-DL-alanine p-toluenesulfonate Chemical compound 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
- 229960003767 alanine Drugs 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000010956 selective crystallization Methods 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 |
|---|---|
| NO752551L true NO752551L (fr) | 1976-02-03 |
Family
ID=23959889
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO752751A NO752551L (fr) | 1974-07-31 | 1975-07-17 |
Country Status (24)
| Country | Link |
|---|---|
| JP (1) | JPS5139626A (fr) |
| AR (1) | AR207648A1 (fr) |
| AU (1) | AU497991B2 (fr) |
| BE (1) | BE831760A (fr) |
| CA (1) | CA1054158A (fr) |
| CH (1) | CH598194A5 (fr) |
| CS (1) | CS191271B2 (fr) |
| DD (1) | DD119209A5 (fr) |
| DE (1) | DE2534031A1 (fr) |
| DK (1) | DK345875A (fr) |
| ES (1) | ES439857A1 (fr) |
| FI (1) | FI752130A (fr) |
| FR (1) | FR2280366A1 (fr) |
| GB (1) | GB1472396A (fr) |
| HU (1) | HU170472B (fr) |
| IE (1) | IE41498B1 (fr) |
| LU (1) | LU73100A1 (fr) |
| NL (1) | NL7508925A (fr) |
| NO (1) | NO752551L (fr) |
| PL (1) | PL103968B1 (fr) |
| SE (1) | SE7508553L (fr) |
| SU (1) | SU568362A3 (fr) |
| YU (1) | YU190675A (fr) |
| ZA (1) | ZA754918B (fr) |
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 (fr) * | 1972-02-03 | 1973-08-07 |
-
1975
- 1975-01-01 AR AR259830A patent/AR207648A1/es active
- 1975-07-17 IE IE1592/75A patent/IE41498B1/en unknown
- 1975-07-17 NO NO752751A patent/NO752551L/no unknown
- 1975-07-21 CA CA231,941A patent/CA1054158A/fr 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 NL NL7508925A patent/NL7508925A/xx not_active Application Discontinuation
- 1975-07-25 BE BE158335A patent/BE831760A/fr not_active IP Right Cessation
- 1975-07-25 YU YU01906/75A patent/YU190675A/xx unknown
- 1975-07-28 SE SE7508553A patent/SE7508553L/xx unknown
- 1975-07-28 GB GB3148875A patent/GB1472396A/en not_active Expired
- 1975-07-29 FR FR7523617A patent/FR2280366A1/fr active Granted
- 1975-07-29 DD DD187544A patent/DD119209A5/xx unknown
- 1975-07-30 SU SU7502163062A patent/SU568362A3/ru active
- 1975-07-30 ES ES439857A patent/ES439857A1/es not_active Expired
- 1975-07-30 ZA ZA754918A patent/ZA754918B/xx unknown
- 1975-07-30 CS CS755338A patent/CS191271B2/cs unknown
- 1975-07-30 DE DE19752534031 patent/DE2534031A1/de active Pending
- 1975-07-30 LU LU73100A patent/LU73100A1/xx unknown
- 1975-07-30 DK DK345875A patent/DK345875A/da unknown
- 1975-07-30 PL PL1975182389A patent/PL103968B1/pl unknown
- 1975-07-31 JP JP50092656A patent/JPS5139626A/ja active Pending
- 1975-07-31 HU HUME1881A patent/HU170472B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU8331675A (en) | 1977-01-27 |
| NL7508925A (nl) | 1976-02-03 |
| DE2534031A1 (de) | 1976-02-12 |
| DD119209A5 (fr) | 1976-04-12 |
| YU190675A (en) | 1984-02-29 |
| FI752130A (fr) | 1976-02-01 |
| LU73100A1 (fr) | 1976-05-31 |
| JPS5139626A (en) | 1976-04-02 |
| ES439857A1 (es) | 1977-06-16 |
| CH598194A5 (fr) | 1978-04-28 |
| DK345875A (da) | 1976-02-01 |
| IE41498B1 (en) | 1980-01-16 |
| PL103968B1 (pl) | 1979-07-31 |
| FR2280366B1 (fr) | 1982-07-30 |
| ZA754918B (en) | 1977-03-30 |
| HU170472B (fr) | 1977-06-28 |
| IE41498L (en) | 1976-01-31 |
| CA1054158A (fr) | 1979-05-08 |
| FR2280366A1 (fr) | 1976-02-27 |
| GB1472396A (en) | 1977-05-04 |
| SU568362A3 (ru) | 1977-08-05 |
| BE831760A (fr) | 1976-01-26 |
| AU497991B2 (en) | 1979-02-01 |
| AR207648A1 (es) | 1976-10-22 |
| CS191271B2 (en) | 1979-06-29 |
| SE7508553L (sv) | 1976-02-02 |
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