JPS6118758A - ４−アセトキシ−ヒドロキシエチルアゼチジン−２−オン誘導体の製造法 - Google Patents
４−アセトキシ−ヒドロキシエチルアゼチジン−２−オン誘導体の製造法Info
- Publication number
- JPS6118758A JPS6118758A JP60004724A JP472485A JPS6118758A JP S6118758 A JPS6118758 A JP S6118758A JP 60004724 A JP60004724 A JP 60004724A JP 472485 A JP472485 A JP 472485A JP S6118758 A JPS6118758 A JP S6118758A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- protecting group
- base
- acetoxy
- 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
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims abstract description 36
- -1 beta-lactam compound Chemical class 0.000 claims abstract description 33
- 125000006239 protecting group Chemical group 0.000 claims abstract description 12
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 239000003960 organic solvent Substances 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 239000000126 substance Substances 0.000 claims abstract description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 6
- 150000008282 halocarbons Chemical class 0.000 claims abstract description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims abstract 2
- 238000004519 manufacturing process Methods 0.000 claims description 13
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 3
- CQXFYUIOYBEJOS-UHFFFAOYSA-N [3-(2-hydroxyethyl)-4-oxoazetidin-2-yl] acetate Chemical class CC(=O)OC1NC(=O)C1CCO CQXFYUIOYBEJOS-UHFFFAOYSA-N 0.000 claims description 3
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical group [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 abstract description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract description 2
- WKDDRNSBRWANNC-ATRFCDNQSA-N Thienamycin Chemical compound C1C(SCCN)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 WKDDRNSBRWANNC-ATRFCDNQSA-N 0.000 abstract 1
- WKDDRNSBRWANNC-UHFFFAOYSA-N Thienamycin Natural products C1C(SCCN)=C(C(O)=O)N2C(=O)C(C(O)C)C21 WKDDRNSBRWANNC-UHFFFAOYSA-N 0.000 abstract 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 28
- 239000000243 solution Substances 0.000 description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
- 239000007788 liquid Substances 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 18
- 239000002904 solvent Substances 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- 235000019341 magnesium sulphate Nutrition 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000012043 crude product Substances 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 150000003952 β-lactams Chemical class 0.000 description 3
- NLRCQIJZKHHOGP-UHFFFAOYSA-N 3-(2-hydroxyethyl)azetidin-2-one Chemical compound OCCC1CNC1=O NLRCQIJZKHHOGP-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 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
- 239000003782 beta lactam antibiotic agent Substances 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000010511 deprotection reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 2
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- 239000002132 β-lactam antibiotic Substances 0.000 description 2
- 229940124586 β-lactam antibiotics Drugs 0.000 description 2
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 1
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 description 1
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 1
- 239000004473 Threonine Substances 0.000 description 1
- 238000006137 acetoxylation reaction Methods 0.000 description 1
- WRYNUJYAXVDTCB-UHFFFAOYSA-M acetyloxymercury Chemical compound CC(=O)O[Hg] WRYNUJYAXVDTCB-UHFFFAOYSA-M 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 125000005103 alkyl silyl group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical class O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 125000003460 beta-lactamyl group Chemical group 0.000 description 1
- MXOSTENCGSDMRE-UHFFFAOYSA-N butyl-chloro-dimethylsilane Chemical compound CCCC[Si](C)(C)Cl MXOSTENCGSDMRE-UHFFFAOYSA-N 0.000 description 1
- YZBQHRLRFGPBSL-RXMQYKEDSA-N carbapenem Chemical compound C1C=CN2C(=O)C[C@H]21 YZBQHRLRFGPBSL-RXMQYKEDSA-N 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229940046892 lead acetate Drugs 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Substances ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- HHXMXAQDOUCLDN-RXMQYKEDSA-N penem Chemical compound S1C=CN2C(=O)C[C@H]21 HHXMXAQDOUCLDN-RXMQYKEDSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- HNOLIWBAJVIBOU-UHFFFAOYSA-N prop-2-enyl 2-chloro-2-oxoacetate Chemical compound ClC(=O)C(=O)OCC=C HNOLIWBAJVIBOU-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 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
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60004724A JPS6118758A (ja) | 1985-01-14 | 1985-01-14 | ４−アセトキシ−ヒドロキシエチルアゼチジン−２−オン誘導体の製造法 |
| CA000485100A CA1256443A (en) | 1984-07-05 | 1985-06-25 | Process for preparing 4-acetoxy-3- hydroxyethylazetidin-2-one derivatives |
| DE8585108208T DE3575128D1 (de) | 1984-07-05 | 1985-07-03 | Verfahren zur herstellung von 4-acetoxy-3-hydroxyethylazetizin-2-on derivaten. |
| SU853923699A SU1442071A3 (ru) | 1984-07-05 | 1985-07-03 | Способ получени производных 4-ацетокси-3-оксиэтилазетидин-2-она (его варианты) |
| EP85108208A EP0167154B1 (en) | 1984-07-05 | 1985-07-03 | Process for preparing 4-acetoxy-3-hydroxyethylazetizin-2-one derivatives |
| ES544864A ES8609238A1 (es) | 1984-07-05 | 1985-07-04 | Un procedimiento para preparar 4-acetoxi-3-hidroxietilazeti-zin-2-ona |
| CN85105098.0A CN1003514B (zh) | 1985-01-14 | 1985-07-04 | 4-乙酰氧基-3-羟基乙基氮杂环丁-2-酮衍生物的制备方法 |
| KR1019850004830A KR900001170B1 (ko) | 1984-07-05 | 1985-07-05 | 4-아세톡시-3-히드록시에틸아제티진-2-온 유도체의 제조방법 |
| US07/000,809 US4861877A (en) | 1984-07-05 | 1987-01-06 | Process for preparing 4-acetoxy-3-hydroxyethylazetidin-2-one derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60004724A JPS6118758A (ja) | 1985-01-14 | 1985-01-14 | ４−アセトキシ−ヒドロキシエチルアゼチジン−２−オン誘導体の製造法 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59139797A Division JPS6118791A (ja) | 1984-07-05 | 1984-07-05 | 新規β−ラクタム化合物及びその製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6118758A true JPS6118758A (ja) | 1986-01-27 |
| JPH0479333B2 JPH0479333B2 (enrdf_load_stackoverflow) | 1992-12-15 |
Family
ID=11591837
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60004724A Granted JPS6118758A (ja) | 1984-07-05 | 1985-01-14 | ４−アセトキシ−ヒドロキシエチルアゼチジン−２−オン誘導体の製造法 |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS6118758A (enrdf_load_stackoverflow) |
| CN (1) | CN1003514B (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62258353A (ja) * | 1986-04-30 | 1987-11-10 | Kanegafuchi Chem Ind Co Ltd | ４−アセトキシ−３−ヒドロキシエチルアゼチジン−２−オン誘導体の製造方法 |
| JPS63239266A (ja) * | 1986-11-13 | 1988-10-05 | Kanegafuchi Chem Ind Co Ltd | ４−アセトキシ−３−ヒドロキシエチルアゼチジン−２−オン誘導体の製造方法 |
| JPS6467A (en) * | 1987-02-20 | 1989-01-05 | Kanegafuchi Chem Ind Co Ltd | Production of 4-acetoxy-3-hydroxyethylazetidin-2-one derivative |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101029056B (zh) * | 2006-02-28 | 2011-06-08 | 天津国韵生物材料有限公司 | 聚-3-羟基丁酸酯在制备β-内酰胺化合物中的用途 |
| CN102491912A (zh) * | 2011-12-28 | 2012-06-13 | 上海新先锋药业有限公司 | N-甲氧基苯基-n-（乙酰）甲基胺合成方法 |
-
1985
- 1985-01-14 JP JP60004724A patent/JPS6118758A/ja active Granted
- 1985-07-04 CN CN85105098.0A patent/CN1003514B/zh not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62258353A (ja) * | 1986-04-30 | 1987-11-10 | Kanegafuchi Chem Ind Co Ltd | ４−アセトキシ−３−ヒドロキシエチルアゼチジン−２−オン誘導体の製造方法 |
| JPS63239266A (ja) * | 1986-11-13 | 1988-10-05 | Kanegafuchi Chem Ind Co Ltd | ４−アセトキシ−３−ヒドロキシエチルアゼチジン−２−オン誘導体の製造方法 |
| JPS6467A (en) * | 1987-02-20 | 1989-01-05 | Kanegafuchi Chem Ind Co Ltd | Production of 4-acetoxy-3-hydroxyethylazetidin-2-one derivative |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1003514B (zh) | 1989-03-08 |
| CN85105098A (zh) | 1986-07-09 |
| JPH0479333B2 (enrdf_load_stackoverflow) | 1992-12-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4914200A (en) | Process for preparing 4-acetoxy-3-hydroxyethylazetidin-2-one derivatives | |
| JPH0586023A (ja) | ベータラクタム抗生物質中間体 | |
| JPH0616622A (ja) | アゼチジノン化合物及びその製造方法 | |
| EP0167154B1 (en) | Process for preparing 4-acetoxy-3-hydroxyethylazetizin-2-one derivatives | |
| FI86852C (fi) | Nya foereningar och foerfarande foer framstaellning av dem | |
| US4138403A (en) | Azabicycloheptanes | |
| JPS6118758A (ja) | ４−アセトキシ−ヒドロキシエチルアゼチジン−２−オン誘導体の製造法 | |
| JPS6284057A (ja) | ４−アセトキシ−３−ヒドロキシエチルアゼチジン−２−オン誘導体の製造法 | |
| JPS62252786A (ja) | ４−置換β−ラクタム化合物 | |
| JPS62195359A (ja) | ４−アセトキシ−３−ヒドロキシエチルアゼチジン−２−オン誘導体の製造方法 | |
| JP2604794B2 (ja) | ４−アセトキシ−３−ヒドロキシエチルアゼチジン−２−オンの製造法 | |
| JPS62164689A (ja) | 新規β−ラクタム化合物及びその製造法 | |
| JPH0267263A (ja) | ４−ベンゾイルオキシ−３−ヒドロキシエチルアゼチジン−２−オン誘導体の製造方法 | |
| US5721360A (en) | Process for the preparation of a thiazoline-azetidinone | |
| JPS62258353A (ja) | ４−アセトキシ−３−ヒドロキシエチルアゼチジン−２−オン誘導体の製造方法 | |
| KR810000713B1 (ko) | 1-옥사데티아세팜 화합물의 제조방법 | |
| JP3213734B2 (ja) | 新規β−ラクタム化合物 | |
| JPH0343278B2 (enrdf_load_stackoverflow) | ||
| JPH045037B2 (enrdf_load_stackoverflow) | ||
| JPH05239020A (ja) | ３−［（ｒ）−１−（置換オキシカルボニルオキシ）エチル−４−置換−２−アゼチジノンの製造法 | |
| JPH0256349B2 (enrdf_load_stackoverflow) | ||
| JPS63239266A (ja) | ４−アセトキシ−３−ヒドロキシエチルアゼチジン−２−オン誘導体の製造方法 | |
| JPS63208569A (ja) | ４−アセトキシ−３−ヒドロキシエチルアゼチジン−２−オン誘導体の製造方法 | |
| JPH085853B2 (ja) | ラクタム化合物およびその製法 | |
| JPS61151190A (ja) | カルバペネム誘導体 |