ES473011A1 - Un procedimiento novedoso para preparar un ester de acido 3-metil-2-(2-clorosulfinil-4-oxo-3-acilamido-1-azetidinil)-3- butenoico - Google Patents
Un procedimiento novedoso para preparar un ester de acido 3-metil-2-(2-clorosulfinil-4-oxo-3-acilamido-1-azetidinil)-3- butenoicoInfo
- Publication number
- ES473011A1 ES473011A1 ES473011A ES473011A ES473011A1 ES 473011 A1 ES473011 A1 ES 473011A1 ES 473011 A ES473011 A ES 473011A ES 473011 A ES473011 A ES 473011A ES 473011 A1 ES473011 A1 ES 473011A1
- Authority
- ES
- Spain
- Prior art keywords
- sulfoxide
- chlorosulfinyl
- intermediates
- chlorosulfinylazetidin
- ones
- 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
- KDXFMMHNGFNJFA-UHFFFAOYSA-N 4-oxoazetidine-2-sulfinyl chloride Chemical class ClS(=O)C1CC(=O)N1 KDXFMMHNGFNJFA-UHFFFAOYSA-N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000000543 intermediate Substances 0.000 abstract 2
- FCZNNHHXCFARDY-WQRUCBPWSA-N (2s,5r,6r)-3,3-dimethyl-4,7-dioxo-6-[(2-phenylacetyl)amino]-4$l^{4}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical class N([C@H]1[C@@H]2N(C1=O)[C@H](C(S2=O)(C)C)C(O)=O)C(=O)CC1=CC=CC=C1 FCZNNHHXCFARDY-WQRUCBPWSA-N 0.000 abstract 1
- 229930186147 Cephalosporin Natural products 0.000 abstract 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 abstract 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 abstract 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 abstract 1
- 239000000292 calcium oxide Substances 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 229940124587 cephalosporin Drugs 0.000 abstract 1
- 150000001780 cephalosporins Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- -1 chlorosulfinyl Chemical group 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- 125000003375 sulfoxide group Chemical group 0.000 abstract 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Un procedimiento nuevo para preparar un éster de ácido 3-metil-2-(2-clorosulfinil-4-oxo-3-acilamino-1-azetidinil)-3-butenoico de fórmula general **(Fórmula)** en donde acilo representa el residuo acilo de un ácido carboxílico, y R1 es un grupo de protección de ácido carboxílico, que se caracteriza por hacer reaccionar a una temperatura entre aproximadamente 70ºC y 120ºC., en condiciones anhidras, en un disolvente inerte un éster de ácido alfa-sulfóxido de 6-acilamido-2,2-dimetilpenam-3-carboxílico con un agente de halogenación de N-cloro en presencia de óxido de alquileno.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/829,689 US4159272A (en) | 1977-09-01 | 1977-09-01 | Process for 2-chlorosulfinylazetidin-4-ones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES473011A1 true ES473011A1 (es) | 1979-10-16 |
Family
ID=25255260
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES473011A Expired ES473011A1 (es) | 1977-09-01 | 1978-08-31 | Un procedimiento novedoso para preparar un ester de acido 3-metil-2-(2-clorosulfinil-4-oxo-3-acilamido-1-azetidinil)-3- butenoico |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US4159272A (es) |
| JP (1) | JPS5446771A (es) |
| AT (1) | AT359079B (es) |
| AU (1) | AU3939078A (es) |
| BE (1) | BE870104A (es) |
| BG (1) | BG30772A3 (es) |
| CA (1) | CA1111049A (es) |
| CS (1) | CS207721B2 (es) |
| DD (1) | DD138546A5 (es) |
| DE (1) | DE2838073A1 (es) |
| DK (1) | DK383978A (es) |
| ES (1) | ES473011A1 (es) |
| FI (1) | FI782657A7 (es) |
| FR (1) | FR2401911A1 (es) |
| GB (1) | GB2003475B (es) |
| GR (1) | GR72458B (es) |
| IL (1) | IL55458A0 (es) |
| IT (1) | IT1099598B (es) |
| NL (1) | NL7808945A (es) |
| NZ (1) | NZ188296A (es) |
| PH (1) | PH15353A (es) |
| PL (1) | PL113056B1 (es) |
| PT (1) | PT68486A (es) |
| RO (1) | RO75128A (es) |
| SE (1) | SE7809202L (es) |
| YU (1) | YU203178A (es) |
| ZA (1) | ZA784981B (es) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4289695A (en) * | 1978-11-13 | 1981-09-15 | Eli Lilly And Company | Process for preparing 2-chlorosulfinylazetidinones |
| US5604222A (en) * | 1993-12-27 | 1997-02-18 | Lupin Laboratories, Ltd. | Method for the preparation of 2-chloro sulfinyl azetidinones |
| US5578721A (en) * | 1994-07-11 | 1996-11-26 | Lupin Laboratories Limited | Process for preparation of 3-exomethylene cepham sulfoxide esters |
| KR100390551B1 (ko) * | 1996-08-22 | 2003-11-17 | 주식회사 코오롱 | 3-할로메틸-3-세펨-4-카르복실레이트 1-옥사이드의 제조방법 |
| CN101190921B (zh) * | 2007-11-27 | 2010-05-19 | 吉林省石油化工设计研究院 | 一种对硝基苄基-7-苯氧基乙酰胺-3-外亚甲基头孢-4-羧酸酯-1-β-氧化物制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3843682A (en) * | 1972-05-15 | 1974-10-22 | Lilly Co Eli | 2-chlorosulfinyl-3-imido-azetedin-4-ones |
| CA1069126A (en) * | 1974-12-24 | 1980-01-01 | Eli Lilly And Company | Sulfinyl halides and their preparation from penicillin sulfoxides |
| US4075203A (en) * | 1976-06-16 | 1978-02-21 | Eli Lilly And Company | Process for preparing a 3-exomethylenecepham sulfoxide from penicillin sulfoxides |
-
1977
- 1977-09-01 US US05/829,689 patent/US4159272A/en not_active Expired - Lifetime
-
1978
- 1978-08-28 YU YU02031/78A patent/YU203178A/xx unknown
- 1978-08-29 RO RO7895061A patent/RO75128A/ro unknown
- 1978-08-29 CA CA310,270A patent/CA1111049A/en not_active Expired
- 1978-08-29 PH PH21543A patent/PH15353A/en unknown
- 1978-08-29 IL IL7855458A patent/IL55458A0/xx unknown
- 1978-08-29 PT PT68486A patent/PT68486A/pt unknown
- 1978-08-30 FR FR7825018A patent/FR2401911A1/fr active Granted
- 1978-08-30 CS CS785624A patent/CS207721B2/cs unknown
- 1978-08-30 DK DK383978A patent/DK383978A/da unknown
- 1978-08-30 NZ NZ188296A patent/NZ188296A/xx unknown
- 1978-08-30 AT AT629178A patent/AT359079B/de active
- 1978-08-30 FI FI782657A patent/FI782657A7/fi unknown
- 1978-08-30 AU AU39390/78A patent/AU3939078A/en active Pending
- 1978-08-30 IT IT27166/78A patent/IT1099598B/it active
- 1978-08-31 DE DE19782838073 patent/DE2838073A1/de not_active Withdrawn
- 1978-08-31 ES ES473011A patent/ES473011A1/es not_active Expired
- 1978-08-31 JP JP10698578A patent/JPS5446771A/ja active Pending
- 1978-08-31 BE BE1009038A patent/BE870104A/xx unknown
- 1978-08-31 PL PL1978209329A patent/PL113056B1/pl unknown
- 1978-08-31 NL NL7808945A patent/NL7808945A/xx not_active Application Discontinuation
- 1978-08-31 ZA ZA784981A patent/ZA784981B/xx unknown
- 1978-08-31 SE SE7809202A patent/SE7809202L/xx unknown
- 1978-09-01 GB GB7835328A patent/GB2003475B/en not_active Expired
- 1978-09-01 DD DD78207609A patent/DD138546A5/xx unknown
- 1978-09-01 BG BG040795A patent/BG30772A3/xx unknown
- 1978-09-29 GR GR57119A patent/GR72458B/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DD138546A5 (de) | 1979-11-07 |
| JPS5446771A (en) | 1979-04-12 |
| CA1111049A (en) | 1981-10-20 |
| GB2003475B (en) | 1982-03-17 |
| BE870104A (fr) | 1979-02-28 |
| NZ188296A (en) | 1981-03-16 |
| IL55458A0 (en) | 1978-10-31 |
| PL113056B1 (en) | 1980-11-29 |
| RO75128A (ro) | 1980-10-30 |
| GR72458B (es) | 1983-11-09 |
| YU203178A (en) | 1982-10-31 |
| NL7808945A (nl) | 1979-03-05 |
| DE2838073A1 (de) | 1979-03-15 |
| ZA784981B (en) | 1980-04-30 |
| FI782657A7 (fi) | 1979-03-02 |
| FR2401911B1 (es) | 1981-03-06 |
| GB2003475A (en) | 1979-03-14 |
| ATA629178A (de) | 1980-03-15 |
| IT7827166A0 (it) | 1978-08-30 |
| AT359079B (de) | 1980-10-27 |
| CS207721B2 (en) | 1981-08-31 |
| IT1099598B (it) | 1985-09-18 |
| DK383978A (da) | 1979-03-02 |
| PT68486A (en) | 1978-09-01 |
| PH15353A (en) | 1982-12-02 |
| SE7809202L (sv) | 1979-03-02 |
| BG30772A3 (bg) | 1981-08-14 |
| US4159272A (en) | 1979-06-26 |
| FR2401911A1 (fr) | 1979-03-30 |
| AU3939078A (en) | 1980-03-06 |
| PL209329A1 (pl) | 1979-06-04 |
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