DE2305187A1 - Verfahren zur auftrennung eines gemisches von 3-fluor-d- und -l-alaninverbindungen - Google Patents
Verfahren zur auftrennung eines gemisches von 3-fluor-d- und -l-alaninverbindungenInfo
- Publication number
- DE2305187A1 DE2305187A1 DE2305187A DE2305187A DE2305187A1 DE 2305187 A1 DE2305187 A1 DE 2305187A1 DE 2305187 A DE2305187 A DE 2305187A DE 2305187 A DE2305187 A DE 2305187A DE 2305187 A1 DE2305187 A1 DE 2305187A1
- Authority
- DE
- Germany
- Prior art keywords
- alanine
- fluoro
- solution
- isomer
- crystals
- 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.)
- Ceased
Links
- 239000000203 mixture Substances 0.000 title claims description 15
- 238000000926 separation method Methods 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 11
- 238000002425 crystallisation Methods 0.000 claims description 26
- 239000000243 solution Substances 0.000 claims description 24
- 230000008025 crystallization Effects 0.000 claims description 20
- 239000013078 crystal Substances 0.000 claims description 14
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 12
- 229950010030 dl-alanine Drugs 0.000 claims description 9
- 229940077388 benzenesulfonate Drugs 0.000 claims description 7
- 239000012452 mother liquor Substances 0.000 claims description 7
- UYTSRQMXRROFPU-UWTATZPHSA-N (2s)-2-amino-3-fluoropropanoic acid Chemical compound FC[C@@H](N)C(O)=O UYTSRQMXRROFPU-UWTATZPHSA-N 0.000 claims description 6
- UYTSRQMXRROFPU-UHFFFAOYSA-N 2-azaniumyl-3-fluoropropanoate Chemical compound FCC(N)C(O)=O UYTSRQMXRROFPU-UHFFFAOYSA-N 0.000 claims description 6
- 229960003767 alanine Drugs 0.000 claims description 6
- XOXBTKOKBQADJP-ARGLLVQISA-N (2S)-2-amino-3-fluoropropanoic acid benzenesulfonic acid Chemical compound C1(=CC=CC=C1)S(=O)(=O)O.FC[C@@H](N)C(=O)O XOXBTKOKBQADJP-ARGLLVQISA-N 0.000 claims description 3
- -1 fluoro-DL-alanine compound Chemical class 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000012047 saturated solution Substances 0.000 claims description 2
- 238000011081 inoculation Methods 0.000 claims 1
- 238000010899 nucleation Methods 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000002002 slurry Substances 0.000 description 5
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 4
- 238000005086 pumping Methods 0.000 description 4
- UYTSRQMXRROFPU-REOHCLBHSA-N (2r)-2-amino-3-fluoropropanoic acid Chemical compound FC[C@H](N)C(O)=O UYTSRQMXRROFPU-REOHCLBHSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000006340 racemization Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000007790 solid phase Substances 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 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 description 1
- DANDTMGGYNCQLG-UHFFFAOYSA-N 4h-1,3-oxazol-5-one Chemical group O=C1CN=CO1 DANDTMGGYNCQLG-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- IOGMRZXPTDCCBW-UHFFFAOYSA-N C(C)(=O)NC(CF)C(=O)O Chemical compound C(C)(=O)NC(CF)C(=O)O IOGMRZXPTDCCBW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 125000003047 N-acetyl group Chemical group 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/36—One oxygen atom
- C07D263/42—One oxygen atom attached in position 5
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 |
|---|---|---|---|
| US22335772A | 1972-02-03 | 1972-02-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2305187A1 true DE2305187A1 (de) | 1973-08-09 |
Family
ID=22836168
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2305187A Ceased DE2305187A1 (de) | 1972-02-03 | 1973-02-02 | Verfahren zur auftrennung eines gemisches von 3-fluor-d- und -l-alaninverbindungen |
Country Status (15)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR207648A1 (es) * | 1974-07-31 | 1976-10-22 | Merck & Co Inc | Procedimiento para resolver una mezcla dl de una sal de 2-deutero-3-fluoro-dl-alanina |
| JPS61152645A (ja) * | 1984-12-27 | 1986-07-11 | Showa Denko Kk | β−クロロ−ＤＬ−アラニンの光学分割方法 |
-
1973
- 1973-01-15 NL NL7300576A patent/NL7300576A/xx not_active Application Discontinuation
- 1973-01-22 CS CS479A patent/CS174867B2/cs unknown
- 1973-01-23 AU AU51371/73A patent/AU472072B2/en not_active Expired
- 1973-01-24 CA CA161,902A patent/CA1001656A/en not_active Expired
- 1973-01-29 GB GB442873A patent/GB1386044A/en not_active Expired
- 1973-01-30 AT AT79173*#A patent/AT329529B/de not_active IP Right Cessation
- 1973-02-01 PL PL1973160524A patent/PL100022B1/pl unknown
- 1973-02-01 SU SU731878075A patent/SU603334A3/ru active
- 1973-02-01 DD DD168608A patent/DD105210A5/xx unknown
- 1973-02-02 CH CH149073A patent/CH591407A5/xx not_active IP Right Cessation
- 1973-02-02 JP JP48013023A patent/JPS4885523A/ja active Pending
- 1973-02-02 HU HUME1597A patent/HU168658B/hu unknown
- 1973-02-02 DE DE2305187A patent/DE2305187A1/de not_active Ceased
- 1973-02-02 FR FR7303667A patent/FR2170181B1/fr not_active Expired
- 1973-02-02 ZA ZA730760A patent/ZA73760B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2170181B1 (enrdf_load_html_response) | 1977-08-19 |
| GB1386044A (en) | 1975-03-05 |
| HU168658B (enrdf_load_html_response) | 1976-06-28 |
| DD105210A5 (enrdf_load_html_response) | 1974-04-12 |
| AT329529B (de) | 1976-05-10 |
| NL7300576A (enrdf_load_html_response) | 1973-08-07 |
| CH591407A5 (enrdf_load_html_response) | 1977-09-15 |
| ATA79173A (de) | 1975-08-15 |
| CS174867B2 (enrdf_load_html_response) | 1977-04-29 |
| ZA73760B (en) | 1974-09-25 |
| CA1001656A (en) | 1976-12-14 |
| JPS4885523A (enrdf_load_html_response) | 1973-11-13 |
| AU472072B2 (en) | 1976-05-13 |
| AU5137173A (en) | 1974-07-25 |
| SU603334A3 (ru) | 1978-04-15 |
| PL100022B1 (pl) | 1978-08-31 |
| FR2170181A1 (enrdf_load_html_response) | 1973-09-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8131 | Rejection |