CN102911134A - Synthesis process for cefditoren pivoxil intermediate - Google Patents
Synthesis process for cefditoren pivoxil intermediate Download PDFInfo
- Publication number
- CN102911134A CN102911134A CN 201110221237 CN201110221237A CN102911134A CN 102911134 A CN102911134 A CN 102911134A CN 201110221237 CN201110221237 CN 201110221237 CN 201110221237 A CN201110221237 A CN 201110221237A CN 102911134 A CN102911134 A CN 102911134A
- Authority
- CN
- China
- Prior art keywords
- methyl
- preparation
- synthesis process
- thiazole
- cefditoren pivoxil
- 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.)
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- RRCLLMUIJYXSGZ-UHFFFAOYSA-N Cc1c(C(OC)=O)[s]cn1 Chemical compound Cc1c(C(OC)=O)[s]cn1 RRCLLMUIJYXSGZ-UHFFFAOYSA-N 0.000 description 1
- JJVIEMFQPALZOZ-UHFFFAOYSA-N Cc1c(C=O)[s]cn1 Chemical compound Cc1c(C=O)[s]cn1 JJVIEMFQPALZOZ-UHFFFAOYSA-N 0.000 description 1
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- Thiazole And Isothizaole Compounds (AREA)
Abstract
The invention relates to a synthesis process for a cefditoren pivoxil intermediate, belongs to the field of drug processing, in particular to the synthesis process for the cefditoren pivoxil intermediate. The synthesis process for the cefditoren pivoxil intermediate has the advantages of simplicity in operation, no pollution and high yield. The process comprises the steps of preparation of 2-amino-4-methyl-5-thiazolecarboxylate; preparation of 4-methyl-5-thiazolecarboxylate; and preparation of 4-methyl-5-formoxyl thiazole.
Description
Technical field:
The invention belongs to the medicine manufacture field, in particular, relate to the synthesis technique of cefditoren intermediate.
Background technology:
4-methyl-5-formyl thiazole is the important side chain of synthetic third generation cephalosporin antibacterial cefditoren, and their molecular structure is as shown below.
The route of synthesis of 4-methyl-5-formyl thiazole is many, mainly is divided into two large classes: (1) is synthetic take 4-methyl-5-thiazole formic acid ester as raw material.The method can be divided into again: catalytic hydrogenation, hydrazine hydrate reduction method and reduction-oxidation method.Catalytic hydrogenation ZrO
2Make catalyzer, high-temperature high-voltage reaction, condition is relatively harsher, and yield is medium, is difficult to realize industrialization; Hydrazine hydrate reduction method step is longer, and yield is not high, does not also have Atom economy.The reduction-oxidation method is the universal method that ester is changed into aldehyde, and Japanese Patent JP45036908 has reported and used LiAlH
4Then ester reduction is oxidized to the method for aldehyde, but LiAlH
4Inflammable, be not suitable for large-scale industrial production.US Patent No. 03/0204095 report NaBH
4System is ester reduction in anhydrous-glyme, and then through hypochlorite oxidation, this reaction solvent must be definitely anhydrous, and aftertreatment is cumbersome, need to consume a large amount of soda acids, and because of solvent and the miscible difficult recovery of water, production cost is higher.(2) other route of synthesis, as: the PDC oxidation style of thiazoleethanol, NBS method, thiazole formonitrile HCN reduction method.The price of thiazoleethanol is lower, and PDC oxidation style reactions steps is short, and reaction yield is medium, is one of method that adopts on the present industrial production.Be difficult to process but the main drawback of PDC oxidation style is the by product chromic salts, cause easily environmental pollution; NBS method synthesis step is longer, and does not have Atom economy; The raw material of thiazole formonitrile HCN reduction method is difficult for obtaining.
Summary of the invention:
The present invention is exactly for the problems referred to above, and a kind of synthesis technique of simple to operate, pollution-free, cefditoren intermediate that productive rate is high is provided.
In order to realize above-mentioned purpose of the present invention, processing step of the present invention is:
1.2-the preparation of amino-4-methyl-5-thiazole formic acid methyl esters
Reaction equation is:
2.4-the preparation of methyl-5-thiazole formic acid methyl esters
Reaction equation is:
3.4-the preparation of methyl-5-formyl thiazole
Reaction equation is:
Beneficial effect of the present invention:
1. the thick product of gained of the present invention is directly used hypochlorite oxidation without separating-purifying, and total recovery is 44%;
2. reaction conditions of the present invention is gentle, and simple to operate, aftertreatment is easy, environmental friendliness.
Embodiment:
Processing step of the present invention is:
1.2-the preparation of amino-4-methyl-5-thiazole formic acid methyl esters
Reaction equation is:
2.4-the preparation of methyl-5-thiazole formic acid methyl esters
Reaction equation is:
3.4-the preparation of methyl-5-formyl thiazole
Reaction equation is:
Product of the present invention has obtained the affirmation of nuclear magnetic spectrogram and mass spectrum.
Claims (1)
1. the synthesis technique of cefditoren intermediate is characterized in that, processing step of the present invention is:
(1) preparation of 2-amino-4-methyl-5-thiazole formic acid methyl esters
Reaction equation is:
(2) preparation of 4-methyl-5-thiazole formic acid methyl esters
Reaction equation is:
(3) preparation of 4-methyl-5-formyl thiazole
Reaction equation is:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201110221237 CN102911134A (en) | 2011-08-04 | 2011-08-04 | Synthesis process for cefditoren pivoxil intermediate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201110221237 CN102911134A (en) | 2011-08-04 | 2011-08-04 | Synthesis process for cefditoren pivoxil intermediate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102911134A true CN102911134A (en) | 2013-02-06 |
Family
ID=47609740
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 201110221237 Pending CN102911134A (en) | 2011-08-04 | 2011-08-04 | Synthesis process for cefditoren pivoxil intermediate |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102911134A (en) |
-
2011
- 2011-08-04 CN CN 201110221237 patent/CN102911134A/en active Pending
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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 |
Application publication date: 20130206 |