JPS59152389A - スルフエンイミン誘導体の製造法 - Google Patents
スルフエンイミン誘導体の製造法Info
- Publication number
- JPS59152389A JPS59152389A JP58025231A JP2523183A JPS59152389A JP S59152389 A JPS59152389 A JP S59152389A JP 58025231 A JP58025231 A JP 58025231A JP 2523183 A JP2523183 A JP 2523183A JP S59152389 A JPS59152389 A JP S59152389A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- general formula
- substituted
- water
- 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.)
- Granted
Links
- -1 beta-lactam compound Chemical class 0.000 claims abstract description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000003960 organic solvent Substances 0.000 claims abstract description 10
- 239000002253 acid Substances 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 239000010410 layer Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000012044 organic layer Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 11
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 150000003842 bromide salts Chemical class 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 150000002148 esters Chemical class 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 16
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 16
- 238000001228 spectrum Methods 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 229910052697 platinum Inorganic materials 0.000 description 8
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 8
- 238000005868 electrolysis reaction Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 230000005611 electricity Effects 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 3
- 229910001623 magnesium bromide Inorganic materials 0.000 description 3
- 101150041968 CDC13 gene Proteins 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- LGLXXNHIGIJYQQ-UHFFFAOYSA-L magnesium;dibromide;hexahydrate Chemical compound O.O.O.O.O.O.[Mg+2].[Br-].[Br-] LGLXXNHIGIJYQQ-UHFFFAOYSA-L 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- LZOZLBFZGFLFBV-UHFFFAOYSA-N sulfene Chemical class C=S(=O)=O LZOZLBFZGFLFBV-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 102100032157 Adenylate cyclase type 10 Human genes 0.000 description 1
- 101000775498 Homo sapiens Adenylate cyclase type 10 Proteins 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000006244 carboxylic acid protecting group Chemical group 0.000 description 1
- 125000001309 chloro group Chemical class Cl* 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000002496 iodine Chemical class 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical group CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical group [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical class [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 150000003952 β-lactams Chemical class 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Cephalosporin Compounds (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58025231A JPS59152389A (ja) | 1983-02-16 | 1983-02-16 | スルフエンイミン誘導体の製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58025231A JPS59152389A (ja) | 1983-02-16 | 1983-02-16 | スルフエンイミン誘導体の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59152389A true JPS59152389A (ja) | 1984-08-31 |
| JPH0561355B2 JPH0561355B2 (enrdf_load_stackoverflow) | 1993-09-06 |
Family
ID=12160195
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58025231A Granted JPS59152389A (ja) | 1983-02-16 | 1983-02-16 | スルフエンイミン誘導体の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59152389A (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62277390A (ja) * | 1985-03-13 | 1987-12-02 | Roller Japan Kk | セフアロスポラン酸誘導体 |
| JP2002105084A (ja) * | 2000-09-29 | 2002-04-10 | Otsuka Chem Co Ltd | ３−セフェム化合物及びその製造法 |
| US10483047B2 (en) | 2016-03-18 | 2019-11-19 | Kabushiki Kaisha Toshiba | Electrochemical reaction device |
-
1983
- 1983-02-16 JP JP58025231A patent/JPS59152389A/ja active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62277390A (ja) * | 1985-03-13 | 1987-12-02 | Roller Japan Kk | セフアロスポラン酸誘導体 |
| JP2002105084A (ja) * | 2000-09-29 | 2002-04-10 | Otsuka Chem Co Ltd | ３−セフェム化合物及びその製造法 |
| US10483047B2 (en) | 2016-03-18 | 2019-11-19 | Kabushiki Kaisha Toshiba | Electrochemical reaction device |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0561355B2 (enrdf_load_stackoverflow) | 1993-09-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2006508898A5 (enrdf_load_stackoverflow) | ||
| US4603014A (en) | Thiazolinoazetidinone derivatives and process for the preparation of the same | |
| JPS59152389A (ja) | スルフエンイミン誘導体の製造法 | |
| JP2000026418A (ja) | ４―フェニル―１，２，３，６―テトラヒドロピリジンの誘導体の新規の製造方法及び用いられる中間体 | |
| JP2648961B2 (ja) | ベンゾチアゾリウム化合物及びその製造方法 | |
| US4532077A (en) | Thiazolineazetidinone-type compounds | |
| JPS60187689A (ja) | ３−エキソメチレンセフアム誘導体の製造法 | |
| CN112359375B (zh) | 一种电化学合成3-烷硒基-4-氨基香豆素化合物的方法 | |
| JPS5874689A (ja) | ３−クロロメチル−３−セフエム誘導体の製造法 | |
| CN112391644B (zh) | 一种二亚砜类化合物的制备方法 | |
| KR860001364B1 (ko) | 7-에피-3-엑소메틸렌 세팜 유도체의 제조방법 | |
| JP2022078673A (ja) | 新規なデヒドロヘテロヘリセン化合物およびその製造方法 | |
| JPH0469353A (ja) | テトラクロル―１，４―ベンゾキノンの製造方法 | |
| JPS59101485A (ja) | アセチジノン誘導体 | |
| CA1249820A (en) | Process for the preparation of 2-¬2-((5- dimethylaminomethyl) furan-2-ylmethylthio) ethylamino|-5-(6-methylpyrid-3-ylmethyl) pyrimid-4-one | |
| JPS6236036B2 (enrdf_load_stackoverflow) | ||
| JP2003517029A (ja) | トリフルオロメチルアセトフェノンの製造方法 | |
| JPH11100376A (ja) | ２，３−ジヒドロベンゾ（ｂ）フラン誘導体および医薬品の製造方法 | |
| JPH01254668A (ja) | バルビツール酸誘導体の電気化学的製造法 | |
| JPS6011486A (ja) | ピペリジリデンメタン第４級塩の製法 | |
| JPH0116917B2 (enrdf_load_stackoverflow) | ||
| JPS5935369B2 (ja) | 光学活性化合物の立体選択的合成法 | |
| JPS58117886A (ja) | ４−置換フエニル酢酸類の製造法 | |
| JPS63211285A (ja) | ２β−置換メチルペニシリン誘導体の製造法 | |
| JPH10251259A (ja) | １，４，６，９−テトラアザ−５，１０−デヒドロフェナジン誘導体及びその製造法 |