IL36552A - The preparation of 4-pyridylthioacetic acid,intermediate for the synthesis of cephalosporin derivatives - Google Patents
The preparation of 4-pyridylthioacetic acid,intermediate for the synthesis of cephalosporin derivativesInfo
- Publication number
- IL36552A IL36552A IL36552A IL3655271A IL36552A IL 36552 A IL36552 A IL 36552A IL 36552 A IL36552 A IL 36552A IL 3655271 A IL3655271 A IL 3655271A IL 36552 A IL36552 A IL 36552A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- acid
- water
- formula
- preparation
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 16
- PGUPJAPHYIEKLT-UHFFFAOYSA-N 2-pyridin-4-ylsulfanylacetic acid Chemical compound OC(=O)CSC1=CC=NC=C1 PGUPJAPHYIEKLT-UHFFFAOYSA-N 0.000 title description 5
- 230000015572 biosynthetic process Effects 0.000 title description 4
- 238000003786 synthesis reaction Methods 0.000 title description 4
- 229930186147 Cephalosporin Natural products 0.000 title description 3
- 229940124587 cephalosporin Drugs 0.000 title description 3
- 150000001780 cephalosporins Chemical class 0.000 title description 3
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 8
- 238000010992 reflux Methods 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 239000002002 slurry Substances 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 3
- ONINFWNBKWMUCA-UHFFFAOYSA-N 2-pyridin-1-ium-4-ylsulfanylacetyl chloride;chloride Chemical compound Cl.ClC(=O)CSC1=CC=NC=C1 ONINFWNBKWMUCA-UHFFFAOYSA-N 0.000 description 3
- -1 4-(l-pyridyl)pyridinium halide Chemical class 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 3
- YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 229940106265 charcoal Drugs 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- IGJFLPNTKLFHMW-UHFFFAOYSA-N 2-pyridin-2-ylsulfanylacetic acid Chemical compound OC(=O)CSC1=CC=CC=N1 IGJFLPNTKLFHMW-UHFFFAOYSA-N 0.000 description 2
- TWUUWLUYSIVBMY-UHFFFAOYSA-N 4-(2h-pyridin-1-yl)pyridin-1-ium;chloride;hydrochloride Chemical compound Cl.[Cl-].C1C=CC=CN1C1=CC=[NH+]C=C1 TWUUWLUYSIVBMY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- QEIOXNYNHNKOLJ-UHFFFAOYSA-N ethyl 2-pyridin-4-ylsulfanylacetate Chemical compound CCOC(=O)CSC1=CC=NC=C1 QEIOXNYNHNKOLJ-UHFFFAOYSA-N 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 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 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Pyridine Compounds (AREA)
- Electric Stoves And Ranges (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2675370A | 1970-04-08 | 1970-04-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL36552A0 IL36552A0 (en) | 1971-08-25 |
| IL36552A true IL36552A (en) | 1974-11-29 |
Family
ID=21833604
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL36552A IL36552A (en) | 1970-04-08 | 1971-04-05 | The preparation of 4-pyridylthioacetic acid,intermediate for the synthesis of cephalosporin derivatives |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US3644377A (en:Method) |
| JP (1) | JPS551253B1 (en:Method) |
| BE (1) | BE765396A (en:Method) |
| CH (1) | CH546761A (en:Method) |
| DE (1) | DE2116159C3 (en:Method) |
| DK (1) | DK140212B (en:Method) |
| ES (1) | ES390039A1 (en:Method) |
| FI (1) | FI52217C (en:Method) |
| FR (1) | FR2089348A5 (en:Method) |
| GB (1) | GB1331718A (en:Method) |
| HU (1) | HU163223B (en:Method) |
| IE (1) | IE35240B1 (en:Method) |
| IL (1) | IL36552A (en:Method) |
| NL (1) | NL7104539A (en:Method) |
| NO (1) | NO133549C (en:Method) |
| PH (1) | PH9953A (en:Method) |
| SE (1) | SE358885B (en:Method) |
| YU (1) | YU34518B (en:Method) |
| ZA (1) | ZA712138B (en:Method) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7317069A (nl) * | 1973-12-13 | 1975-06-17 | Oce Andeno Bv | Werkwijze voor de bereiding van al of niet ge- substitueerd 4-pyridylthioazijnzuur. |
| GB2122603A (en) * | 1982-06-25 | 1984-01-18 | Lark Spa | 7-Ä???-(substituted-thio)-acylamidoÜ-cephalosporanic acids |
| CN117343003A (zh) * | 2023-09-13 | 2024-01-05 | 河北远征药业有限公司 | 一种头孢匹林中间体的合成方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2330641A (en) * | 1940-11-20 | 1943-09-28 | Lederle Lab Inc | Preparation of 4-pyridine sulphonic acid |
| DE1225178B (de) * | 1956-12-21 | 1966-09-22 | Boehringer Sohn Ingelheim | Verfahren zur Herstellung von 4-Mercaptopyridinen sowie von deren Alkyl- oder Alkenylaethern |
-
1970
- 1970-04-08 US US26753A patent/US3644377A/en not_active Expired - Lifetime
-
1971
- 1971-03-31 IE IE416/71A patent/IE35240B1/xx unknown
- 1971-04-01 SE SE04237/71A patent/SE358885B/xx unknown
- 1971-04-02 DE DE2116159A patent/DE2116159C3/de not_active Expired
- 1971-04-02 ZA ZA712138A patent/ZA712138B/xx unknown
- 1971-04-05 FI FI710954A patent/FI52217C/fi active
- 1971-04-05 PH PH12343A patent/PH9953A/en unknown
- 1971-04-05 NL NL7104539A patent/NL7104539A/xx unknown
- 1971-04-05 NO NO1309/71A patent/NO133549C/no unknown
- 1971-04-05 IL IL36552A patent/IL36552A/en unknown
- 1971-04-05 DK DK160671AA patent/DK140212B/da not_active IP Right Cessation
- 1971-04-06 BE BE765396A patent/BE765396A/xx not_active IP Right Cessation
- 1971-04-06 JP JP2077571A patent/JPS551253B1/ja active Pending
- 1971-04-06 HU HUBI393A patent/HU163223B/hu unknown
- 1971-04-07 FR FR7112344A patent/FR2089348A5/fr not_active Expired
- 1971-04-07 YU YU865/71A patent/YU34518B/xx unknown
- 1971-04-07 ES ES390039A patent/ES390039A1/es not_active Expired
- 1971-04-08 CH CH511871A patent/CH546761A/xx not_active IP Right Cessation
- 1971-04-19 GB GB2642171*A patent/GB1331718A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IL36552A0 (en) | 1971-08-25 |
| US3644377A (en) | 1972-02-22 |
| IE35240B1 (en) | 1975-12-24 |
| CH546761A (de) | 1974-03-15 |
| NL7104539A (en:Method) | 1971-10-12 |
| DE2116159A1 (de) | 1971-11-11 |
| SE358885B (en:Method) | 1973-08-13 |
| FR2089348A5 (en:Method) | 1972-01-07 |
| DE2116159B2 (de) | 1980-11-06 |
| YU86571A (en) | 1979-02-28 |
| YU34518B (en) | 1979-09-10 |
| NO133549C (en:Method) | 1976-05-19 |
| IE35240L (en) | 1971-10-08 |
| ES390039A1 (es) | 1973-06-01 |
| JPS551253B1 (en:Method) | 1980-01-12 |
| DK140212B (da) | 1979-07-09 |
| PH9953A (en) | 1976-06-14 |
| BE765396A (fr) | 1971-10-06 |
| DK140212C (en:Method) | 1979-12-03 |
| ZA712138B (en) | 1971-12-29 |
| NO133549B (en:Method) | 1976-02-09 |
| DE2116159C3 (de) | 1987-12-03 |
| FI52217C (fi) | 1977-07-11 |
| GB1331718A (en) | 1973-09-26 |
| HU163223B (en:Method) | 1973-07-28 |
| FI52217B (en:Method) | 1977-03-31 |
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