DE1950391A1 - Verfahren zur Herstellung von 7-Aminocephalosporansaeure - Google Patents
Verfahren zur Herstellung von 7-AminocephalosporansaeureInfo
- Publication number
- DE1950391A1 DE1950391A1 DE19691950391 DE1950391A DE1950391A1 DE 1950391 A1 DE1950391 A1 DE 1950391A1 DE 19691950391 DE19691950391 DE 19691950391 DE 1950391 A DE1950391 A DE 1950391A DE 1950391 A1 DE1950391 A1 DE 1950391A1
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- mixture
- dimethoxypropane
- aca
- quenching
- 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
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 title claims description 29
- 238000000034 method Methods 0.000 title claims description 18
- 238000002360 preparation method Methods 0.000 title claims description 4
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 claims description 27
- HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 239000011541 reaction mixture Substances 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 16
- 238000010791 quenching Methods 0.000 claims description 16
- HOKIDJSKDBPKTQ-GLXFQSAKSA-N Cephalosporin C Natural products S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(O)=O)[C@@H]12 HOKIDJSKDBPKTQ-GLXFQSAKSA-N 0.000 claims description 14
- HOKIDJSKDBPKTQ-GLXFQSAKSA-M cephalosporin C(1-) Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H]([NH3+])C([O-])=O)[C@@H]12 HOKIDJSKDBPKTQ-GLXFQSAKSA-M 0.000 claims description 14
- 230000000171 quenching effect Effects 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000002837 carbocyclic group Chemical group 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 2
- 230000000802 nitrating effect Effects 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
- 239000004157 Nitrosyl chloride Substances 0.000 description 8
- VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 description 8
- 235000019392 nitrosyl chloride Nutrition 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical group [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- 239000000908 ammonium hydroxide Substances 0.000 description 5
- 238000003776 cleavage reaction Methods 0.000 description 5
- 235000019253 formic acid Nutrition 0.000 description 5
- 125000004971 nitroalkyl group Chemical group 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 230000007017 scission Effects 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229930186147 Cephalosporin Natural products 0.000 description 3
- 229940124587 cephalosporin Drugs 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 150000001780 cephalosporins Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical compound CCC[N+]([O-])=O JSZOAYXJRCEYSX-UHFFFAOYSA-N 0.000 description 1
- FGLBSLMDCBOPQK-UHFFFAOYSA-N 2-nitropropane Chemical compound CC(C)[N+]([O-])=O FGLBSLMDCBOPQK-UHFFFAOYSA-N 0.000 description 1
- 241000252073 Anguilliformes Species 0.000 description 1
- 101100074846 Caenorhabditis elegans lin-2 gene Proteins 0.000 description 1
- -1 Cephalosporin compound Chemical class 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
- 101100497386 Mus musculus Cask gene Proteins 0.000 description 1
- 229910020175 SiOH Inorganic materials 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/18—7-Aminocephalosporanic or substituted 7-aminocephalosporanic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US76564068A | 1968-10-07 | 1968-10-07 | |
| US78724768A | 1968-12-26 | 1968-12-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1950391A1 true DE1950391A1 (de) | 1970-10-08 |
Family
ID=27117629
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691950391 Pending DE1950391A1 (de) | 1968-10-07 | 1969-10-06 | Verfahren zur Herstellung von 7-Aminocephalosporansaeure |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS4927197B1 (enExample) |
| CH (1) | CH519518A (enExample) |
| DE (1) | DE1950391A1 (enExample) |
| FR (1) | FR2020062A1 (enExample) |
| GB (1) | GB1277228A (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5248297U (enExample) * | 1975-10-01 | 1977-04-06 | ||
| US6518420B2 (en) | 1997-06-04 | 2003-02-11 | Biochemie Gesellschaft M.B.H. | Precipitation process of 7-aminocephalosporanic acid (7-ACA) |
| BR9809916A (pt) * | 1997-06-04 | 2000-10-03 | Biochemie Gmbh | Processo de precipitação melhorada de ácido 7-aminocefalosporânico (7-aca) |
-
1969
- 1969-10-06 GB GB4906769A patent/GB1277228A/en not_active Expired
- 1969-10-06 DE DE19691950391 patent/DE1950391A1/de active Pending
- 1969-10-06 JP JP7924969A patent/JPS4927197B1/ja active Pending
- 1969-10-07 FR FR6934128A patent/FR2020062A1/fr not_active Withdrawn
- 1969-10-07 CH CH1505269A patent/CH519518A/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH519518A (de) | 1972-02-29 |
| GB1277228A (en) | 1972-06-07 |
| FR2020062A1 (enExample) | 1970-07-10 |
| JPS4927197B1 (enExample) | 1974-07-16 |
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