JPS6146A - ジヒドロキシフエニルグリシン塩及びその製法 - Google Patents
ジヒドロキシフエニルグリシン塩及びその製法Info
- Publication number
- JPS6146A JPS6146A JP60115196A JP11519685A JPS6146A JP S6146 A JPS6146 A JP S6146A JP 60115196 A JP60115196 A JP 60115196A JP 11519685 A JP11519685 A JP 11519685A JP S6146 A JPS6146 A JP S6146A
- Authority
- JP
- Japan
- Prior art keywords
- dihydroxyphenylglycine
- salt
- optically active
- bromocamphor
- acid
- 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.)
- Pending
Links
- HOOWCUZPEFNHDT-ZETCQYMHSA-N (S)-3,5-dihydroxyphenylglycine Chemical class OC(=O)[C@@H](N)C1=CC(O)=CC(O)=C1 HOOWCUZPEFNHDT-ZETCQYMHSA-N 0.000 title claims description 30
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 150000003839 salts Chemical class 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 22
- ZBWTWPZGSGMRTG-UHFFFAOYSA-N 2-azaniumyl-2-(3,4-dihydroxyphenyl)acetate Chemical compound OC(=O)C(N)C1=CC=C(O)C(O)=C1 ZBWTWPZGSGMRTG-UHFFFAOYSA-N 0.000 claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- 239000013078 crystal Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- 238000010956 selective crystallization Methods 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 229960000583 acetic acid Drugs 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 239000012452 mother liquor Substances 0.000 claims description 4
- 239000002798 polar solvent Substances 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 239000012362 glacial acetic acid Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 3
- NJQADTYRAYFBJN-UHFFFAOYSA-N 2-bromo-4,7,7-trimethylbicyclo[2.2.1]heptan-3-one Chemical compound C1CC2(C)C(=O)C(Br)C1C2(C)C NJQADTYRAYFBJN-UHFFFAOYSA-N 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- RXSPMCUQMQOINZ-UHFFFAOYSA-N 2-(3,4-dihydroxyanilino)acetic acid Chemical compound OC(=O)CNC1=CC=C(O)C(O)=C1 RXSPMCUQMQOINZ-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 3
- 229930186147 Cephalosporin Chemical class 0.000 description 3
- 229930182555 Penicillin Natural products 0.000 description 3
- 229940124587 cephalosporin Drugs 0.000 description 3
- 150000001780 cephalosporins Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical class N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical class C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- 229940049954 penicillin Drugs 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- ZBWTWPZGSGMRTG-SSDOTTSWSA-N (2r)-2-azaniumyl-2-(3,4-dihydroxyphenyl)acetate Chemical class OC(=O)[C@H](N)C1=CC=C(O)C(O)=C1 ZBWTWPZGSGMRTG-SSDOTTSWSA-N 0.000 description 1
- IXWOUPGDGMCKGT-UHFFFAOYSA-N 2,3-dihydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1O IXWOUPGDGMCKGT-UHFFFAOYSA-N 0.000 description 1
- WHCPMOJDSBYNAN-UHFFFAOYSA-N 2-amino-2-(2,4-dihydroxyphenyl)acetic acid Chemical compound OC(=O)C(N)C1=CC=C(O)C=C1O WHCPMOJDSBYNAN-UHFFFAOYSA-N 0.000 description 1
- YJVLTUAAYZRZML-UHFFFAOYSA-N 2-amino-2-(2,5-dihydroxyphenyl)acetic acid Chemical compound OC(=O)C(N)C1=CC(O)=CC=C1O YJVLTUAAYZRZML-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 238000003916 acid precipitation Methods 0.000 description 1
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 description 1
- 235000008206 alpha-amino acids Nutrition 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000008054 sulfonate salts Chemical class 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8413652 | 1984-05-29 | ||
| GB848413652A GB8413652D0 (en) | 1984-05-29 | 1984-05-29 | Chemical process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6146A true JPS6146A (ja) | 1986-01-06 |
Family
ID=10561623
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60115196A Pending JPS6146A (ja) | 1984-05-29 | 1985-05-28 | ジヒドロキシフエニルグリシン塩及びその製法 |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0164026A1 (en]) |
| JP (1) | JPS6146A (en]) |
| AU (1) | AU4305485A (en]) |
| ES (1) | ES8606248A1 (en]) |
| GB (1) | GB8413652D0 (en]) |
| GR (1) | GR851297B (en]) |
| ZA (1) | ZA853993B (en]) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5310427A (en) * | 1990-08-03 | 1994-05-10 | Japan Airlines Co., Ltd. | Method for transporting live fish |
-
1984
- 1984-05-29 GB GB848413652A patent/GB8413652D0/en active Pending
-
1985
- 1985-05-22 EP EP85106310A patent/EP0164026A1/en not_active Withdrawn
- 1985-05-27 GR GR851297A patent/GR851297B/el unknown
- 1985-05-27 ZA ZA853993A patent/ZA853993B/xx unknown
- 1985-05-28 ES ES543570A patent/ES8606248A1/es not_active Expired
- 1985-05-28 JP JP60115196A patent/JPS6146A/ja active Pending
- 1985-05-28 AU AU43054/85A patent/AU4305485A/en not_active Abandoned
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5310427A (en) * | 1990-08-03 | 1994-05-10 | Japan Airlines Co., Ltd. | Method for transporting live fish |
| US5572952A (en) * | 1990-08-03 | 1996-11-12 | Japan Airlines Co., Ltd. | Method for transporting live fish and container for use in the same |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA853993B (en) | 1986-04-30 |
| ES543570A0 (es) | 1986-04-01 |
| GB8413652D0 (en) | 1984-07-04 |
| AU4305485A (en) | 1985-12-05 |
| GR851297B (en]) | 1985-11-25 |
| ES8606248A1 (es) | 1986-04-01 |
| EP0164026A1 (en) | 1985-12-11 |
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