CN107739321A - The preparation method of the sulfonic acid aminobutyric acid of 2 amino 3 - Google Patents
The preparation method of the sulfonic acid aminobutyric acid of 2 amino 3 Download PDFInfo
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- CN107739321A CN107739321A CN201710867686.8A CN201710867686A CN107739321A CN 107739321 A CN107739321 A CN 107739321A CN 201710867686 A CN201710867686 A CN 201710867686A CN 107739321 A CN107739321 A CN 107739321A
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- CN
- China
- Prior art keywords
- amino
- sulfonic acid
- preparation
- acid
- aminobutyric acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/34—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfuric acids
Abstract
The present invention relates to a kind of preparation method of the sulfonic acid aminobutyric acid of 2 amino 3, water is added into reactor and is warming up to 40-70 DEG C, addition (3S is trans) -3- amino -4- methyl -2- oxos -1- azetidins alkyl sulfonic acid and catalyst are stirred, insulation reaction；Then acidizing reagent is added, is cooled to 0-5 DEG C, suction filtration obtains crystalline powder 2- amino -3- sulfonic acid aminobutyric acids.The simple to operate, high income of the present invention, cost are low, easily controllable, operation cycle is short, mechanism and performance of the 2- amino -3- sulfonic acid aminobutyric acids that can be prepared by using the present invention etc. are analyzed the impurity of AZT main ring, so as to reach the effect for improving AZT main ring purity.
Description
Technical field
The present invention relates to a kind of preparation method of 2- amino -3- sulfonic acid aminobutyric acids, belong to medical synthesis field.
Background technology
AZT is monocyclic beta-lactam class antibiotic, has good therapeutic effect to gram positive bacterial infection.Ammonia is bent
Southern main ring ((3S- is trans) -3- amino -4- methyl -2- oxo -1- azetidins alkyl sulfonic acid) is the important centre for synthesizing AZT
Body, its quality and purity directly affect the quality of cefotaxime active ester, and then influence quality and the life of cefotaxime medicine
Produce cost.At present because the purity of AZT main ring is relatively low, main cause generates the production of open loop final production in building-up process
Thing 2- amino -3- sulfonic acid aminobutyric acids, because the material is similar to AZT main ring polarity, it is difficult to separation and synthesis, have impact on
The analysis of AZT main ring purity and the purification of product.Control to impurity in AZT main ring at present is to separation without related
Report document.
The content of the invention
It is an object of the invention to provide a kind of preparation method of 2- amino -3- sulfonic acid aminobutyric acids, simple to operate, yield
Height, cost are low, easily controllable, and the operation cycle is short, the 2- amino -3- sulfonic acid aminobutyric acids that can be prepared by using the present invention
Mechanism and performance etc. are analyzed the impurity of AZT main ring, so as to reach the effect for improving AZT main ring purity.
The preparation method of 2- amino -3- sulfonic acid aminobutyric acids, water is added into reactor and is warming up to 40-70 DEG C, addition
(3S- is trans) -3- amino -4- methyl -2- oxos -1- azetidins alkyl sulfonic acid and catalyst are stirred, insulation reaction；Then
Acidizing reagent is added, is cooled to 0-5 DEG C, suction filtration obtains crystalline powder 2- amino -3- sulfonic acid aminobutyric acids.
Catalyst is triethylamine, sodium hydroxide, potassium hydroxide, sodium carbonate and/or ammoniacal liquor.Preferentially select triethylamine.
The dosage of catalyst is (3S- is trans) -3- amino -4- methyl -2- oxo -1- azetidin alkyl sulfonic acid quality
5%-20%.
The mass ratio of water and (3S- is trans) -3- amino -4- methyl -2- oxo -1- azetidin alkyl sulfonic acids is 4:1-7:1.
Holding temperature is 40-70 DEG C.
The time of stirring reaction is 30-120min.
The acidizing reagent of addition is hydrochloric acid, sulfuric acid, acetic acid or ethanedioic acid.
The acidizing reagent regulation pH=1-3 of addition.
Compared with prior art, the invention has the advantages that：
The preparation method of 2- amino -3- sulfonic acid aminobutyric acids of the present invention, simple to operate, high income, cost are low, are easy to control
System, the operation cycle is short, and mechanism and performance of the 2- amino -3- sulfonic acid aminobutyric acids that can be prepared by using the present invention etc. are to ammonia
The impurity of bent southern main ring is analyzed, so as to reach the effect for improving AZT main ring purity.
Embodiment
The present invention is described further with reference to embodiment.
Embodiment 1
300kg water is added into 500L reactors and is warming up to 40 DEG C, adds (3S- is trans) -3- amino -4- methyl -2- oxygen
Generation -1- azetidin alkyl sulfonic acid 100kg and triethylamine 20kg regulation PH to 9.2 ± 0.2, stirs 30min, then adds hydrochloric acid and adjust
PH=3 is saved, is cooled to 0 DEG C of crystallization 1h, filters, obtains product purity 99.5%.
Embodiment 2
300kg water is added into 500L reactors and is warming up to 40 DEG C, adds (3S- is trans) -3- amino -4- methyl -2- oxygen
Generation -1- azetidin alkyl sulfonic acid 100kg and triethylamine about 20kg regulation PH to 9.2 ± 0.2, stirs 30min, then adds hydrochloric acid
PH=1 is adjusted, is cooled to 0-5 DEG C of crystallization 1h, filters, obtains product purity 99.5%.
Embodiment 3
300kg water is added into 500L reactors and is warming up to 40 DEG C, adds (3S- is trans) -3- amino -4- methyl -2- oxygen
Generation -1- azetidin alkyl sulfonic acid 100kg and potassium hydroxide about 18kg regulation PH to 9.2 ± 0.2, stirs 30min, then adds salt
Acid for adjusting pH=2,0-5 DEG C of crystallization 1h is cooled to, filters, obtain product purity 99.5%.
Embodiment 4
300kg water is added into 500L reactors and is warming up to 40 DEG C, adds (3S- is trans) -3- amino -4- methyl -2- oxygen
Generation -1- azetidin alkyl sulfonic acid 100kg and sodium hydroxide about 17.5kg regulation PH to 9.2 ± 0.2, stirs 30min, then adds
Hydrochloric acid adjusts pH=3, is cooled to 0-5 DEG C of crystallization 1h, filters, obtains product purity 99.5%.
Embodiment 5
300kg water is added into 500L reactors and is warming up to 40 DEG C, adds (3S- is trans) -3- amino -4- methyl -2- oxygen
Generation -1- azetidin alkyl sulfonic acid 100kg and sodium carbonate 20kg, then liquid feeding alkali regulation PH to 9.2 ± 0.2, stir 30min, then
Hydrochloric acid regulation pH=2 is added, 0-5 DEG C of crystallization 1h is cooled to, filters, obtain product purity 99.5%.
Claims (8)
1. a kind of preparation method of 2- amino -3- sulfonic acid aminobutyric acids, it is characterised in that add water into reactor and be warming up to
40-70 DEG C, add (3S- is trans) -3- amino -4- methyl -2- oxos -1- azetidins alkyl sulfonic acid and catalyst be stirred,
Insulation reaction；Then acidizing reagent is added, is cooled to 0-5 DEG C, suction filtration obtains crystalline powder 2- amino -3- sulfonic acid amino fourths
Acid.
2. the preparation method of 2- amino -3- sulfonic acid aminobutyric acids according to claim 1, it is characterised in that catalyst is
Triethylamine, sodium hydroxide, potassium hydroxide, sodium carbonate and/or ammoniacal liquor.
3. the preparation method of 2- amino -3- sulfonic acid aminobutyric acids according to claim 1, it is characterised in that catalyst
Dosage is the 5%-20% of (3S- is trans) -3- amino -4- methyl -2- oxo -1- azetidin alkyl sulfonic acid quality.
4. the preparation method of 2- amino -3- sulfonic acid aminobutyric acids according to claim 1, it is characterised in that water and (3S-
It is trans) mass ratioes of -3- amino -4- methyl -2- oxo -1- azetidin alkyl sulfonic acids is 4:1-7:1.
5. the preparation method of 2- amino -3- sulfonic acid aminobutyric acids according to claim 1, it is characterised in that holding temperature
For 40-70 DEG C.
6. the preparation method of 2- amino -3- sulfonic acid aminobutyric acids according to claim 1, it is characterised in that stirring reaction
Time be 30-120min.
7. the preparation method of 2- amino -3- sulfonic acid aminobutyric acids according to claim 1, it is characterised in that the acid of addition
Change reagent is hydrochloric acid, sulfuric acid, acetic acid or ethanedioic acid.
8. the preparation method of 2- amino -3- sulfonic acid aminobutyric acids according to claim 7, it is characterised in that the acid of addition
Change reagent regulation pH=1-3.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710867686.8A CN107739321A (en) | 2017-09-22 | 2017-09-22 | The preparation method of the sulfonic acid aminobutyric acid of 2 amino 3 |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710867686.8A CN107739321A (en) | 2017-09-22 | 2017-09-22 | The preparation method of the sulfonic acid aminobutyric acid of 2 amino 3 |
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| CN107739321A true CN107739321A (en) | 2018-02-27 |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000012466A1 (en) * | 1998-08-26 | 2000-03-09 | Glaxo Group Limited | Formamide compounds as therapeutic agents |
| WO2000063165A1 (en) * | 1999-04-19 | 2000-10-26 | Fujisawa Pharmaceutical Co., Ltd. | Mmp inhibitor |
| CN103044416A (en) * | 2012-12-17 | 2013-04-17 | 浙江华方药业有限责任公司 | Synthetic method of Carumonam sodium |
| WO2014165746A1 (en) * | 2013-04-05 | 2014-10-09 | The University Of Chicago | Methods and compositions using adam10 inhibitors to treat bacterial infections |
| CN106831523A (en) * | 2017-02-09 | 2017-06-13 | 四川同晟生物医药有限公司 | The preparation method of 3 hydroxy azetidine hydrochlorides and the hydroxy azetidines of N Boc 3 |
-
2017
- 2017-09-22 CN CN201710867686.8A patent/CN107739321A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000012466A1 (en) * | 1998-08-26 | 2000-03-09 | Glaxo Group Limited | Formamide compounds as therapeutic agents |
| WO2000063165A1 (en) * | 1999-04-19 | 2000-10-26 | Fujisawa Pharmaceutical Co., Ltd. | Mmp inhibitor |
| CN103044416A (en) * | 2012-12-17 | 2013-04-17 | 浙江华方药业有限责任公司 | Synthetic method of Carumonam sodium |
| WO2014165746A1 (en) * | 2013-04-05 | 2014-10-09 | The University Of Chicago | Methods and compositions using adam10 inhibitors to treat bacterial infections |
| CN106831523A (en) * | 2017-02-09 | 2017-06-13 | 四川同晟生物医药有限公司 | The preparation method of 3 hydroxy azetidine hydrochlorides and the hydroxy azetidines of N Boc 3 |
Non-Patent Citations (2)
| Title |
|---|
| CONSTANTINE G. BOOJAMRA ET AL: "Stereochemical Elucidation and Total Synthesis of Dihydropacidamycin D, a Semisynthetic Pacidamycin", 《J. AM. CHEM. SOC》 * |
| 陈兴鹏等: "非对称氮杂环丁烷的区域选择性开环反应", 《化学进展》 * |
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Application publication date: 20180227 |