CN1552700A - Synthesis of benzothiazole active ester - Google Patents
Synthesis of benzothiazole active ester Download PDFInfo
- Publication number
- CN1552700A CN1552700A CNA031316484A CN03131648A CN1552700A CN 1552700 A CN1552700 A CN 1552700A CN A031316484 A CNA031316484 A CN A031316484A CN 03131648 A CN03131648 A CN 03131648A CN 1552700 A CN1552700 A CN 1552700A
- Authority
- CN
- China
- Prior art keywords
- active ester
- thiazole
- benzene
- pair
- catalyzer
- 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.)
- Pending
Links
Landscapes
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
A low cost process for preparing the active benzothiazine ester as the intermediate of cephalo-type antibiotics features that the cheap triethyl phosphite is used as its catalyst.
Description
Technical field
The invention relates to producing cephalosporin antibiotic medicine intermediate---the improvement of benzene a pair of horses going side by side thiazole active ester synthetic method relates in particular to a kind of low cost production benzene a pair of horses going side by side thiazole active ester synthetic method.
Background technology
Benzene a pair of horses going side by side thiazole active ester MEAM (chemical name: 2-methoxyimino-2-(thiazolamine base)-(Z)-thioacetic acid benzene a pair of horses going side by side thiazole, English name: 2-(2-Aminothiazol-4-y1)-2-syn-methoximinoacetic acid 2-benzothiazolyl thioester is called for short the AE active ester), be to be used to produce cephalosporin antibiotic, as main raw materials such as rocephin, cefotaxime sodiums.Usually synthetic method such as US4767852 are open, by ainothiazoly loximate, curing Dibenzo thiazole (being called for short DM promotor), and synthetic forming under triphenyl phosphorus catalysis, its synthetic equation is as follows:
Yet this with triphenyl phosphorus catalyst synthetic method, because the catalyzer triphenyl phosphorus costs an arm and a leg, cause production cost higher; Secondly, the triphenyl phosphorus molecular weight is bigger, and making the reaction large usage quantity has also increased production cost.
The invention technology
The objective of the invention is to overcome the deficiency of above-mentioned prior art, the benzene a pair of horses going side by side thiazole active ester synthetic method that provides a kind of production cost that bigger reduction is arranged.
The object of the invention realizes that main the improvement is the triethyl-phosphite that adopts relative low price through screening, replaces the triphenyl phosphorus catalyzer, descends thereby production cost is had by a relatively large margin.Specifically, benzene a pair of horses going side by side thiazole active ester synthetic method of the present invention comprises that the catalysis under catalyzer of ainothiazoly loximate, curing Dibenzo thiazole is synthetic, it is characterized in that said catalyzer is a triethyl-phosphite.Soon through redox reaction, reaction equation is as follows by mole ratio for ainothiazoly loximate, curing Dibenzo thiazole (DM), triethyl-phosphite:
The present invention is owing to select for use the low triethyl-phosphite of price as synthetic catalyst, and synthetic benzene a pair of horses going side by side thiazole active ester not only makes the catalyzer cost adopt triphenyl phosphorus to reduce greatly, and the catalyzer cost only is original 1/4; And because triethyl-phosphite molecular weight (166) is much smaller than triphenyl phosphorus molecular weight (262), therefore under same mol condition, participate in chemical reaction, the triphenyl phosphorus consumption is required to be 1.58 times of triethyl-phosphite, adopt triethyl-phosphite can reduce the catalyzer consumption greatly again thus, catalyst consumption only is about 63% of a triphenyl phosphorus.By existing city price, only catalyst consumption is about more than 80% with regard to escapable cost.And its reaction by-product can be recycled, and more can reduce the production cost of benzene a pair of horses going side by side thiazole active ester greatly.
Below in conjunction with an indefiniteness embodiment, further specify the inventive method.
Embodiment
Embodiment: with 8 kilograms of triethyl-phosphites, 12 kilograms of curing Dibenzo thiazoles, the 120 kg methylene dichloride, in stirring at room about 30 minutes, be cooled to 0 ℃, slowly add 6.7 kilograms of ainothiazoly loximates, and keep about 0 ℃, stirred 3.5-4 hour solid.With 50 kilograms of ethyl acetate agitator treating after-filtration, again with the ethyl acetate washing, get benzene a pair of horses going side by side thiazole active ester, fusing point 128-130 ℃, (tetrahydrofuran (THF)/methylene dichloride).
Claims (1)
1, a kind of benzene a pair of horses going side by side thiazole active ester synthetic method comprises that the catalysis under catalyzer of ainothiazoly loximate, curing Dibenzo thiazole is synthetic, it is characterized in that said catalyzer is a triethyl-phosphite.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA031316484A CN1552700A (en) | 2003-05-30 | 2003-05-30 | Synthesis of benzothiazole active ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA031316484A CN1552700A (en) | 2003-05-30 | 2003-05-30 | Synthesis of benzothiazole active ester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1552700A true CN1552700A (en) | 2004-12-08 |
Family
ID=34322933
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA031316484A Pending CN1552700A (en) | 2003-05-30 | 2003-05-30 | Synthesis of benzothiazole active ester |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1552700A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1321989C (en) * | 2005-06-23 | 2007-06-20 | 浙江工业大学 | AE-active ester chemical synthesizing method |
| CN100448856C (en) * | 2006-06-26 | 2009-01-07 | 山东金城医药化工股份有限公司 | New technique for catalytic synthesis of AE active ester |
| CN101747291B (en) * | 2009-12-22 | 2011-06-22 | 山东鑫泉医药中间体有限公司 | Method for synthesizing AE-active ester |
| CN104387337A (en) * | 2014-12-15 | 2015-03-04 | 山东鑫泉医药有限公司 | Method for synthesizing 3-ethyl-2-sulfur ethyl benzothiazole perchlorate by AE (Active Ester) residues |
| CN107903179A (en) * | 2017-11-23 | 2018-04-13 | 淄博鑫泉医药技术服务有限公司 | The method that triethylamine and triethyl phosphate are recycled from AE active ester mother liquors |
-
2003
- 2003-05-30 CN CNA031316484A patent/CN1552700A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1321989C (en) * | 2005-06-23 | 2007-06-20 | 浙江工业大学 | AE-active ester chemical synthesizing method |
| CN100448856C (en) * | 2006-06-26 | 2009-01-07 | 山东金城医药化工股份有限公司 | New technique for catalytic synthesis of AE active ester |
| CN101747291B (en) * | 2009-12-22 | 2011-06-22 | 山东鑫泉医药中间体有限公司 | Method for synthesizing AE-active ester |
| CN104387337A (en) * | 2014-12-15 | 2015-03-04 | 山东鑫泉医药有限公司 | Method for synthesizing 3-ethyl-2-sulfur ethyl benzothiazole perchlorate by AE (Active Ester) residues |
| CN107903179A (en) * | 2017-11-23 | 2018-04-13 | 淄博鑫泉医药技术服务有限公司 | The method that triethylamine and triethyl phosphate are recycled from AE active ester mother liquors |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101550110B (en) | Preparation method of D-threo-2-(dichloromethyl)-4, 5-dihydro-5-(p-(methylsulfonyl) phenyl)-4-oxazole methanol | |
| CN1552700A (en) | Synthesis of benzothiazole active ester | |
| CN110697758B (en) | Method for constructing multilevel-structure copper sulfide nanoenzyme by biological template method | |
| CN101405252A (en) | Fullerene derivative and method for producing same | |
| TW200615298A (en) | Process for producing polytrimethylene rephthalate | |
| CN1394863A (en) | Method for synthesizing cefotaxime sodium | |
| US10316012B1 (en) | Method of synthesizing (1S, 5R)-lactone | |
| MXPA03008645A (en) | Process for the industrial synthesis of the methyl diester of 5-amino-3-carboxymethyl-4-cyano-2-thiophenecarboxylic acid, and application to the synthesis of bivalent salts of ranelic acid and their hydrates. | |
| CN1282377A (en) | Process for preparation of beta-lactam antibiotic | |
| CN107513047B (en) | Green process for synthesizing ceftazidime side chain acid active ester by microwave-assisted method | |
| CN107686557A (en) | A kind of preparation method and applications of enzyme crosslinking hydrogel | |
| CN1696113A (en) | Stereoselectivity technique for synthesizing nitrogen heterocycle butanone | |
| CN104263772B (en) | A kind of method that acetyl phosphate is prepared based on biology enzyme | |
| CN1087350C (en) | Process for enzymatic synthesis of beta-lactam antibiotics in presence of enzyme inhibitor | |
| CN106518865A (en) | Method for preparing 1-alkenyl indolizine derivative | |
| CN102336721A (en) | Method for synthesizing AE-active ester by using water-containing 2-(2-amino-4-thiazolyl)-2-(Z)-methoxyimino acetic acid | |
| CN1634932A (en) | Process for preparing cefotaxime sodium | |
| CN112279288A (en) | Continuous preparation method of modified calcium sulfate | |
| CN86103304A (en) | The preparation method of 2-carboxyl pyrazine-4-oxide compound | |
| EP1564217A3 (en) | Process for the production of epothilones | |
| CN108484526A (en) | A kind of method of ester-interchange method synthesis AE active ester | |
| CN108822057A (en) | A kind of synthetic method of AE active ester | |
| CN108017658A (en) | A kind of synthetic method of Cefprozil | |
| CN113481253B (en) | Method for preparing pyridoxal phosphate by biocatalysis | |
| EP0650963A1 (en) | Improved process for the preparation of 2-methylthiazole-5-carboxylates |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |