CN104592083A - Method for preparing N-acetyl-DL-thioproline - Google Patents
Method for preparing N-acetyl-DL-thioproline Download PDFInfo
- Publication number
- CN104592083A CN104592083A CN201510014625.8A CN201510014625A CN104592083A CN 104592083 A CN104592083 A CN 104592083A CN 201510014625 A CN201510014625 A CN 201510014625A CN 104592083 A CN104592083 A CN 104592083A
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- CN
- China
- Prior art keywords
- acetyl
- thioproline
- acetic acid
- acid
- diacetyl oxide
- 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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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Abstract
The invention relates to a method for preparing N-acetyl-DL-thioproline. The method comprises the following steps: taking a proper amount of N-acetyl-L-thioproline, adding acetic acid, dissolving, heating, adding acetic anhydride, keeping temperature at 90 DEG.C, standing for 3.5 hours, racemizing, recycling acetic acid under reduced pressure, adding water, catching acid, cooling, crystallizing and drying. N-acetyl-L-thioproline is used as raw material and dissolved by using acetic acid, 1-2mol of acetic anhydride is used for racemizing at 80-100 DEG.C to avoid the production of byproducts, the acetic acid recycling rate is high, the production links are reduced, and alkali is prevented from participating in the reaction.
Description
Technical field
The present invention relates to a kind of amino acid whose preparation method, especially a kind of preparation method of N-acetyl-DL-Thioproline.
Background technology
Amino acid is the common name of the class organic compound containing amino and carboxyl.The basic composition unit of biological function macro-molecular protein is the base substance forming Animal nutrition desired protein, is the organic compound containing a basic amine group and an acidic carboxypolymer.Amino acid whose kind is more; for N-acetyl-DL-Thioproline; the preparation method of present N-acetyl-DL-Thioproline mainly passes through L-Thioproline in acidity, high temperature and salicylic aldehyde racemization; then acid crystal is caught up with; acidylate and obtaining in the basic conditions, L-Thioproline is at acid, high temperature and by product aftertreatment trouble is produced in the easy open loop of salicylic aldehyde racemization and yield is low.
Summary of the invention
The object of the invention is, in order to the defect solved in prior art existing for the preparation of N-acetyl-DL-Thioproline, to provide a kind of preparation method of N-acetyl-DL-Thioproline.
To achieve these goals, the technical solution used in the present invention is:
Prepare a method for N-acetyl-DL-Thioproline, comprise the steps:
Get appropriate N-acetyl-L-Thioproline, add acetic acid and heat, adding diacetyl oxide, temperature keeps 90 degree, and shelve racemization after 3.5 hours, reclaim under reduced pressure acetic acid, adds water, catches up with acid, and crystallisation by cooling is also dried.
The above-mentioned method preparing N-acetyl-DL-Thioproline, the temperature of described Racemic of N controls at 80 DEG C---and 110 DEG C.
The above-mentioned method preparing N-acetyl-DL-Thioproline, the concentration of described diacetyl oxide is 1-2mol.
The above-mentioned method preparing N-acetyl-DL-Thioproline, the volume ratio of described acetic acid and diacetyl oxide is 10: 1.
Beneficial effect of the present invention is: the present invention is from N-acetyl-L-Thioproline, and with acetic acid, use 1-2mol diacetyl oxide, racemization under 80-100 degree, avoid the generation of by product, acetic acid recovery utilization rate is high, reduces production link, removes alkali from and participates in reaction.
Embodiment
Further understand for making to have constitutional features of the present invention and effect of reaching and be familiar with, in order to preferred embodiment detailed description, be described as follows:
Example 1:
100g N-acetyl-L-PROLINE, add 800ml acetic acid and be warming up to 90 degree of dissolvings, add 80ML diacetyl oxide keep 90 degree 3.5 hours, recording optically-active is 0, reclaim under reduced pressure acetic acid 800ML, the 500ML water that adds water catches up with acid, concentrated 120ML, is cooled to 4 degree, crystallization, suction filtration obtains mother liquor 20ML, dries to obtain 80gN-acetyl-DL-Thioproline.
Example 2:
100gN-acetyl-L-PROLINE, add 800ml reclaim acetic acid be warming up to 95 degree of dissolving, add 75ML diacetyl oxide maintenance 90 degree 3.5 hours, recording optically-active is 0, reclaim under reduced pressure acetic acid 800ML, the 500ML water that adds water catches up with acid, adds mother liquor 20ML, concentrated 120ML, be cooled to 4 degree, crystallization, the mother liquor 20ML of suction filtration, dries to obtain 90gN-acetyl-DL-Thioproline.
Example 3:
100gN-acetyl-L-PROLINE, add 800ml reclaim acetic acid be warming up to 90 degree of dissolving, add 85ML diacetyl oxide maintenance 90 degree 3.5 hours, recording optically-active is 0, reclaim under reduced pressure acetic acid 800ML, the 500ML water that adds water catches up with acid, adds mother liquor 20ML, concentrated 120ML, be cooled to 4 degree, crystallization, the mother liquor 20ML of suction filtration, dries to obtain 90gN-acetyl-DL-Thioproline.
More than show and describe ultimate principle of the present invention, principal character and advantage of the present invention.The technician of the industry should understand; the present invention is not restricted to the described embodiments; the just principle of the present invention described in above-described embodiment and specification sheets; the present invention also has various changes and modifications without departing from the spirit and scope of the present invention, and these changes and improvements all fall in claimed scope of the present invention.The protection domain of application claims is defined by appending claims and equivalent thereof.
Claims (4)
1. prepare a method for N-acetyl-DL-Thioproline, it is characterized in that, comprise the steps:
Get appropriate N-acetyl-L-Thioproline, add acetic acid and heat, adding diacetyl oxide, temperature keeps 90 degree, and shelve racemization after 3.5 hours, reclaim under reduced pressure acetic acid, adds water, catches up with acid, and crystallisation by cooling is also dried.
2. the method preparing N-acetyl-DL-Thioproline according to claim 1, is characterized in that, the temperature of described Racemic of N controls at 80 DEG C---110 DEG C.
3. the method preparing N-acetyl-DL-Thioproline according to claim 1, is characterized in that, the concentration of described diacetyl oxide is 1-2mol.
4. the method preparing N-acetyl-DL-Thioproline according to claim 1, is characterized in that, the volume ratio of described acetic acid and diacetyl oxide is 10: 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510014625.8A CN104592083A (en) | 2015-01-06 | 2015-01-06 | Method for preparing N-acetyl-DL-thioproline |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510014625.8A CN104592083A (en) | 2015-01-06 | 2015-01-06 | Method for preparing N-acetyl-DL-thioproline |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN104592083A true CN104592083A (en) | 2015-05-06 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510014625.8A Pending CN104592083A (en) | 2015-01-06 | 2015-01-06 | Method for preparing N-acetyl-DL-thioproline |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113439743A (en) * | 2021-06-25 | 2021-09-28 | 河南科技学院 | Growth regulator composition containing sodium salicylate and hemiphyllin |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4738965Y1 (en) * | 1968-12-03 | 1972-11-25 | ||
| DE3325667A1 (en) * | 1982-09-07 | 1984-03-08 | Etablissements Mesnel S.A., 78420 Carrières-sur-Seine | EXTRUDED SEAL |
| CN1213400A (en) * | 1996-03-13 | 1999-04-07 | 隆萨股份公司 | Process for producing N-protected D-proline derivatives |
| CN1569815A (en) * | 2004-04-29 | 2005-01-26 | 何佺 | Amino acid racemization method |
| CN1680282A (en) * | 2005-01-24 | 2005-10-12 | 南京大学 | Microwave depsun method of photo-active amino acid or salt thereof |
| WO2009065797A1 (en) * | 2007-11-23 | 2009-05-28 | Universitat De Lleida | Process for obtaining mixtures of 4-carboxy-1,3-thiazolidinium carboxylate and n-acyl-1,3-thiazolidin-4-carboxylic acid |
| CN101863818A (en) * | 2010-06-30 | 2010-10-20 | 宜兴市前成生物有限公司 | Method for preparing DL-proline |
| CN102234252A (en) * | 2010-05-05 | 2011-11-09 | 张永昶 | Preparation method of bioregulator folcisteine |
-
2015
- 2015-01-06 CN CN201510014625.8A patent/CN104592083A/en active Pending
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4738965Y1 (en) * | 1968-12-03 | 1972-11-25 | ||
| DE3325667A1 (en) * | 1982-09-07 | 1984-03-08 | Etablissements Mesnel S.A., 78420 Carrières-sur-Seine | EXTRUDED SEAL |
| CN1213400A (en) * | 1996-03-13 | 1999-04-07 | 隆萨股份公司 | Process for producing N-protected D-proline derivatives |
| CN1569815A (en) * | 2004-04-29 | 2005-01-26 | 何佺 | Amino acid racemization method |
| CN1680282A (en) * | 2005-01-24 | 2005-10-12 | 南京大学 | Microwave depsun method of photo-active amino acid or salt thereof |
| WO2009065797A1 (en) * | 2007-11-23 | 2009-05-28 | Universitat De Lleida | Process for obtaining mixtures of 4-carboxy-1,3-thiazolidinium carboxylate and n-acyl-1,3-thiazolidin-4-carboxylic acid |
| CN102234252A (en) * | 2010-05-05 | 2011-11-09 | 张永昶 | Preparation method of bioregulator folcisteine |
| CN101863818A (en) * | 2010-06-30 | 2010-10-20 | 宜兴市前成生物有限公司 | Method for preparing DL-proline |
Non-Patent Citations (4)
| Title |
|---|
| 何佺，等: "氨基酸的消旋研究", 《氨基酸和生物资源》 * |
| 何佺，等: "脯氨酸的消旋研究", 《华东理工大学学报》 * |
| 彭阳峰，等: "2-(4-氯苯基)-3-甲基丁酸的消旋", 《合成化学》 * |
| 王家荣，等: "L-酪氨酸的消旋研究", 《高等化学工程学报》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113439743A (en) * | 2021-06-25 | 2021-09-28 | 河南科技学院 | Growth regulator composition containing sodium salicylate and hemiphyllin |
| CN113439743B (en) * | 2021-06-25 | 2022-04-15 | 河南科技学院 | Growth regulator composition containing sodium salicylate and hemiphyllin |
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Application publication date: 20150506 |