JPH0158189B2 - - Google Patents
Info
- Publication number
- JPH0158189B2 JPH0158189B2 JP56044854A JP4485481A JPH0158189B2 JP H0158189 B2 JPH0158189 B2 JP H0158189B2 JP 56044854 A JP56044854 A JP 56044854A JP 4485481 A JP4485481 A JP 4485481A JP H0158189 B2 JPH0158189 B2 JP H0158189B2
- Authority
- JP
- Japan
- Prior art keywords
- singlet
- group
- ethyl acetate
- carboxylic acid
- general formula
- 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.)
- Expired
Links
- -1 benzenesulfonylamino group Chemical group 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 150000008282 halocarbons Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 238000000034 method Methods 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 125000002252 acyl group Chemical group 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 125000003277 amino group Chemical group 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 235000002639 sodium chloride Nutrition 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 238000006884 silylation reaction Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XOHZHMUQBFJTNH-UHFFFAOYSA-N 1-methyl-2h-tetrazole-5-thione Chemical compound CN1N=NN=C1S XOHZHMUQBFJTNH-UHFFFAOYSA-N 0.000 description 1
- ALCKLBOCZKLPJN-UHFFFAOYSA-N 3-cyanopropanethioyl chloride Chemical compound ClC(=S)CCC#N ALCKLBOCZKLPJN-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- FEZFGJCSBWYLCC-UHFFFAOYSA-N dicyclohexylazanium;bromide Chemical compound Br.C1CCCCC1NC1CCCCC1 FEZFGJCSBWYLCC-UHFFFAOYSA-N 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Landscapes
- Cephalosporin Compounds (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4485481A JPS57159789A (en) | 1981-03-27 | 1981-03-27 | Preparation of cephamycin derivative |
| DK075582A DK162603C (da) | 1981-02-23 | 1982-02-22 | Fremgangsmaade til fremstilling af beta-lactam-antibiotica |
| CH108282A CH646977A5 (en) | 1981-02-23 | 1982-02-22 | Process for the preparation of derivatives of beta-lactam antibiotics |
| SE8201087A SE452620B (sv) | 1981-02-23 | 1982-02-22 | Forfarande for framstellning av derivat av beta-laktamantibiotika |
| NL8200708A NL8200708A (nl) | 1981-02-23 | 1982-02-23 | Werkwijze voor de bereiding van beta-lactamantibioticaverbindingen. |
| ES509837A ES509837A0 (es) | 1981-02-23 | 1982-02-23 | Un procedimiento para preparar derivados de antibioticos-lactamicos. |
| CA000396796A CA1194470A (en) | 1981-02-23 | 1982-02-23 | PROCESS FOR PREPARING DERIVATIVES OF .beta.-LACTAM ANTI- BIOTICS |
| IT67194/82A IT1157951B (it) | 1981-02-23 | 1982-02-23 | Procedimento per la preparazione di antibiotici betalattamici |
| FI820582A FI72521C (fi) | 1981-02-23 | 1982-02-23 | Foerfarande foer framstaellning av cefalosporinderivat. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4485481A JPS57159789A (en) | 1981-03-27 | 1981-03-27 | Preparation of cephamycin derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57159789A JPS57159789A (en) | 1982-10-01 |
| JPH0158189B2 true JPH0158189B2 (fi) | 1989-12-11 |
Family
ID=12703064
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4485481A Granted JPS57159789A (en) | 1981-02-23 | 1981-03-27 | Preparation of cephamycin derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57159789A (fi) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5520723A (en) * | 1978-08-02 | 1980-02-14 | Nippon Kayaku Co Ltd | Preparation of cephalosporin compound |
-
1981
- 1981-03-27 JP JP4485481A patent/JPS57159789A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5520723A (en) * | 1978-08-02 | 1980-02-14 | Nippon Kayaku Co Ltd | Preparation of cephalosporin compound |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57159789A (en) | 1982-10-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2005526049A (ja) | ベンゾイソキサゾールメタンスルホニルクロリドの調製及びゾニスアミドを形成するためのそのアミド化の方法 | |
| JP2973143B2 (ja) | ３−アシルアミノ−６−フェニルオキシ−７−アルキルスルホニルアミノ−４ｈ−１−ベンゾピラン−４−オンまたはその塩の製造法 | |
| JPH0141152B2 (fi) | ||
| JPH0158189B2 (fi) | ||
| JP2826646B2 (ja) | ３−置換−５−ハロゲノピリジン誘導体 | |
| JPH058200B2 (fi) | ||
| JPS6310707B2 (fi) | ||
| JP2957699B2 (ja) | ７α―アルコキシセフェム誘導体の製造方法 | |
| JPS6053039B2 (ja) | Ｎ−アセチル／イラミン酸誘導体およびその製造方法 | |
| JP3059007B2 (ja) | １−（２−カルボキシフェニル）インダゾール誘導体の製造方法 | |
| JP2763214B2 (ja) | Ｌ−プロリン誘導体の製造法 | |
| JPS6121638B2 (fi) | ||
| KR100241089B1 (ko) | 2-메르캅토-4-메틸-1,3-티아졸-5-아세트산의 신규한제조방법 | |
| KR900003882B1 (ko) | H₂항히스타민 활성을 갖는 화합물의 제조방법 | |
| EP0060301A1 (en) | Process for preparing cephalosporin compounds | |
| JPH0812658A (ja) | シドノン類の製造法 | |
| JPS6145639B2 (fi) | ||
| JPS6287599A (ja) | エリスロマイシン類のオキシム誘導体の製造法 | |
| KR820000785B1 (ko) | 1-(테트라하이드로-2-푸라닐)-5-플루오로우라실의 제조법 | |
| JPH10287657A (ja) | 放射線増感剤の製造方法 | |
| JPS6213936B2 (fi) | ||
| JPS61172846A (ja) | （±）−２−クロロプロピオン酸の光学分割法 | |
| KR100238645B1 (ko) | 세팔로스포린 유도체의 새로운 에스테르화 방법 | |
| CH617704A5 (fi) | ||
| JPH02233692A (ja) | 新規なｎ↑６，２′―ｏ―ジ置換―アデノシン―３′，５′―環状リン酸及びその製法 |