CN104003890B - A kind of method for preparing the phenylpropionic acid of 3 amino of S or R types optical isomer 3 - Google Patents
A kind of method for preparing the phenylpropionic acid of 3 amino of S or R types optical isomer 3 Download PDFInfo
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Abstract
The invention discloses a kind of method for preparing the phenylpropionic acid of 3 amino of S or R types optical isomer 3, wherein R or S represent chiral centre configuration, include the preparation of the phenylpropionic acid camphorsulfonic acid double salt of 3 amino of step 1) S or R type optical isomer 3；2) free hydrolysis；The phenylpropionic acid camphorsulfonic acid double salt of 3 amino of S or R types optical isomer 3 is filtrated to get the phenylpropionic acid of 3 amino of the S or R types optical isomer 3 after peracid or alkali free hydrolysis, raw materials used and resolution reagent is cheap and easy to get, chiral induction body can be with Reusability, the three wastes are few, and three skill greatly simplify, can obtain simultaneously S or R type optical isomers compound, cost it is low, be adapted to industrialized production.
Description
Technical field
The present invention relates to chemical field, more particularly to one kind to prepare S or R type optical isomer 3- amino -3- phenylpropionic acids
Method.
Background technology
Amino -3- the phenylpropionic acids of optically active isomer S types optically active isomer 3 are that synthesis antidepressant reaches Bo Xi
Amino -3- the phenylpropionic acids of spit of fland important intermediate R types optically active isomer 3 are also the important intermediate for synthesizing multi-medicament.It
The method for splitting of preceding report mainly must be by being split again by enzymatic clarification, chemical resolution after changing structure or derivative
Return to its low length in configuration technique road, agents useful for same is expensive to be not easy to obtain, cost is high, the three wastes are more, low yield, technological requirement height not
Easily industrialization large-scale production.
The content of the invention
The technical problems to be solved by the invention are to provide the system that a kind of cost is low, the three wastes are few, yield is high, technological requirement is low
The method of standby S or R type optical isomer 3- amino -3- phenylpropionic acids.
In order to solve the above technical problems, the technical scheme is that：One kind prepare S or R type optical isomer 3- amino-
The method of 3- phenylpropionic acids, wherein R or S represent chiral centre configuration, comprise the following steps：
1) preparation of the amino -3- phenylpropionic acid camphorsulfonic acid double salt of S or R types optical isomer 3
Racemic modification 3- amino -3- phenylpropionic acids are added in water, acetic acid, alcohol solvent with chiral reagent and are warmed to
50-80 DEG C of reaction 10-30 minute, 5-20 DEG C is cooled to afterwards, add chiral shift reagent and place crystallization, be filtrated to get S or R types
Amino -3- phenylpropionic acid camphorsulfonic acid the double salt of optical isomer 3；
2) free hydrolysis
By the amino -3- phenylpropionic acid camphorsulfonic acid double salt of S or R types optical isomer 3 mistake after peracid or alkali free hydrolysis
Filter obtains S the or R types optical isomer 3- amino -3- phenylpropionic acids.
As preferable technical scheme, the chiral reagent includes optically active camphorsulfonic acid, bromo-camphor sulfonic acid, chlorine camphor tree
Brain sulfonic acid.
The preparation of the amino -3- phenylpropionic acid camphorsulfonic acid double salt of S types optical isomer 3：
Amino -3- the phenylpropionic acids of racemic 3 are added in 250ml reaction bulbs：Water, acetic acid, ethanol, camphorsulfonic acid heating
50-80 DEG C of reaction 10-30 minute, it is cooled to 5-20 DEG C and adds chiral shift reagent placement crystallization, be filtrated to get S type optical siomerisms
Amino -3- phenylpropionic acid camphorsulfonic acid the double salt of body 3.
The preparation of the amino -3- phenylpropionic acid camphorsulfonic acid double salt of R types optical isomer 3：
Amino -3- the phenylpropionic acids of racemic 3, water, acetic acid, ethanol, bromo-camphor sulfonic acid are added in 250ml reaction bulbs, is added
Warm 50-80 DEG C of reaction 10-30 minute is cooled to 5-20 DEG C of addition chiral shift reagent placement and is filtrated to get R types optical isomer 3
Amino -3- phenylpropionic acid double salt.
As preferable technical scheme, the mol ratio of the chiral reagent and the racemic modification is 0.5~1.5:1.
As preferable technical scheme, the chiral shift reagent includes camphorsulfonic acid neighbour's chlorobenzene sweet acid salt, bromo-camphor
Sulfonic acid hydroxyphenylglycine salt, chlorcamphor sulfonic acid aminophenyl propionate.
As preferable technical scheme, the chiral shift reagent and the racemic modification mol ratio be 0.001~
0.005：1.
As preferable technical scheme, the free hydrolysis in the step 2) includes the amino -3- benzene of S types optical isomer 3
Base propionic acid camphorsulfonic acid double salt free hydrolysis and the amino -3- phenylpropionic acid camphorsulfonic acid double salt free waters of R types optical isomer 3
Solution.
As preferable technical scheme, the amino -3- phenylpropionic acid camphorsulfonic acid double salt of S types optical isomer 3 dissociates
It is hydrolyzed to and adds the amino -3- phenylpropionic acid camphorsulfonic acids double salt of S types optical isomer 3, and is with mass concentration under agitation
10% ammoniacal liquor regulation PH is 7-8, and cooling placement 5 hours, filter to obtain the amino -3- phenyl third of S types optical isomer 3 at 10 DEG C
Acid.
As preferable technical scheme, the amino -3- phenylpropionic acid camphorsulfonic acid double salt of R types optical isomer 3 dissociates
It is hydrolyzed to and adds the amino -3- phenylpropionic acid camphorsulfonic acids double salt of R types optical isomer 3, and is with mass concentration under agitation
10% ammoniacal liquor regulation PH is 9-10, and filter liquor is adjusted back PH to 2-3 with the hydrochloric acid of mass concentration 10%, carried with dichloromethane
Take, dried without small magnesium sulfate, cooling is concentrated at 5-10 DEG C, is filtrated to get the R types optical isomer 3- amino -3- phenyl third
Acid.
Amino -3- the phenylpropionic acids of S or R types optical isomer 3 are pharmaceutical intermediate Dapoxetine hydrochloride or similar medicine
Applied in synthesis.
A kind of by adopting the above-described technical solution, side for preparing S or R type optical isomer 3- amino -3- phenylpropionic acids
Method, wherein R or S represent chiral centre configuration, including the amino -3- phenylpropionic acid camphor sulphurs of step 1) S or R type optical isomer 3
The preparation of sour double salt；Racemic modification 3- amino -3- phenylpropionic acids and chiral reagent are added in water, acetic acid, alcohol solvent and added
Temperature is cooled to 5-20 DEG C, adds chiral shift reagent and place crystallization, be filtrated to get S afterwards to 50-80 DEG C of reaction 10-30 minute
Or amino -3- phenylpropionic acid camphorsulfonic acid the double salt of R types optical isomer 3；2) free hydrolysis；By the ammonia of S or R types optical isomer 3
Base -3- phenylpropionic acid camphorsulfonic acid double salt is filtrated to get S the or R types optical isomer 3- ammonia after peracid or alkali free hydrolysis
Base -3- phenylpropionic acids, raw materials used and resolution reagent is cheap and easy to get, and chiral induction body can be with Reusability, and the three wastes are few, Er Qiesan
Skill greatly simplifies, can obtain simultaneously S or R type optical isomers compound, cost it is low, be adapted to industrialized production.
Embodiment
With reference to embodiment, the present invention is expanded on further.It should be understood that these embodiments be merely to illustrate the present invention without
For limiting the scope of the present invention.In addition, it is to be understood that after the content of the invention lectured has been read, those skilled in the art can
To be made various changes or modifications to the present invention, these equivalent form of values equally fall within the model that the application appended claims are limited
Enclose.
A kind of method for preparing S or R type optical isomer 3- amino -3- phenylpropionic acids, wherein R or S represent chiral centre
Configuration, comprise the following steps：
1) preparation of the amino -3- phenylpropionic acid camphorsulfonic acid double salt of S or R types optical isomer 3
Racemic modification 3- amino -3- phenylpropionic acids are added in water, acetic acid, alcohol solvent with chiral reagent and are warmed to
50-80 DEG C of reaction 10-30 minute, 5-20 DEG C is cooled to afterwards, add chiral shift reagent and place crystallization, be filtrated to get S or R types
Amino -3- phenylpropionic acid camphorsulfonic acid the double salt of optical isomer 3；
2) free hydrolysis
By the amino -3- phenylpropionic acid camphorsulfonic acid double salt of S or R types optical isomer 3 mistake after peracid or alkali free hydrolysis
Filter obtains S the or R types optical isomer 3- amino -3- phenylpropionic acids.
As preferable technical scheme, the chiral reagent includes optically active camphorsulfonic acid, bromo-camphor sulfonic acid, chlorine camphor tree
Brain sulfonic acid.
The preparation of the amino -3- phenylpropionic acid camphorsulfonic acid double salt of S types optical isomer 3：
Amino -3- the phenylpropionic acids of racemic 3 are added in 250ml reaction bulbs：Water, acetic acid, ethanol, camphorsulfonic acid heating
50-80 DEG C of reaction 10-30 minute, it is cooled to 5-20 DEG C and adds chiral shift reagent placement crystallization, be filtrated to get S type optical siomerisms
Amino -3- phenylpropionic acid camphorsulfonic acid the double salt of body 3.
The preparation of the amino -3- phenylpropionic acid camphorsulfonic acid double salt of R types optical isomer 3：
Amino -3- the phenylpropionic acids of racemic 3, water, acetic acid, ethanol, bromo-camphor sulfonic acid are added in 250ml reaction bulbs, is added
Warm 50-80 DEG C of reaction 10-30 minute is cooled to 5-20 DEG C of addition chiral shift reagent placement and is filtrated to get R types optical isomer 3
Amino -3- phenylpropionic acid double salt.
The mol ratio of the chiral reagent and the racemic modification is 0.5~1.5:1.
The chiral shift reagent include camphorsulfonic acid neighbour's chlorobenzene sweet acid salt, bromo-camphor sulfonic acid hydroxyphenylglycine salt,
Chlorcamphor sulfonic acid aminophenyl propionate.
The chiral shift reagent is 0.001~0.005 with the racemic modification mol ratio：1.
The free hydrolysis stated in step 2) dissociates including the amino -3- phenylpropionic acid camphorsulfonic acid double salt of S types optical isomer 3
Hydrolysis and the amino -3- phenylpropionic acid camphorsulfonic acid double salt free hydrolysis of R types optical isomer 3.
Amino -3- phenylpropionic acid camphorsulfonic acid double salt the free hydrolysis of S types optical isomer 3 is by S type optical siomerisms
Amino -3- phenylpropionic acid camphorsulfonic acids the double salt of body 3 adds, and the ammoniacal liquor regulation PH for being under agitation 10% with mass concentration is 7-
8, cooling placement 5 hours, filter to obtain the amino -3- phenylpropionic acids of S types optical isomer 3 at 10 DEG C.
Amino -3- phenylpropionic acid camphorsulfonic acid double salt the free hydrolysis of R types optical isomer 3 is by R type optical siomerisms
Amino -3- phenylpropionic acid camphorsulfonic acids the double salt of body 3 adds, and the ammoniacal liquor regulation PH for being under agitation 10% with mass concentration is 9-
10, filter liquor adjusts back PH to 2-3 with the hydrochloric acid of mass concentration 10%, is extracted with dichloromethane, is dried without small magnesium sulfate, 5-10
Cooling is concentrated at DEG C, is filtrated to get the R types optical isomer 3- amino -3- phenylpropionic acids.
Amino -3- the phenylpropionic acids of S or R types optical isomer 3 are pharmaceutical intermediate Dapoxetine hydrochloride or similar medicine
Applied in synthesis.
Embodiment one：
16.6g3- amino -3- phenylpropionic acids, 23.5g camphorsulfonic acids are added in 250ml single port bottles add water 16.6ml,
Ethanol 0.46ml, acetic acid 0.6ml, heating reaction 15 minutes, naturally cool to 5-20 DEG C at 50-80 DEG C, add 0.418g hands
Property induction agent place 20h crystallize slowly, be filtrated to get white crystal 15g and then recrystallize to obtain solid crystal 14g.
Solids 14g adds with regulation PH to the 9-10 filterings of 10% ammonia spirit under water 28g stirrings, and filtrate is again with 10% hydrochloric acid
PH to 2-3 is adjusted, is extracted with 40*2ml dichloros alkane, is dried without small magnesium sulfate, is concentrated to give white solid 4.2g yields 73%.
The of embodiment two
16.6g3- amino -3- benzenpropanoic acids, bromo-camphor sulfonic acid 32.9g are added in 250ml single port bottles, add water 16.6ml, second
Alcohol 0.46ml, acetic acid 0.6ml, 15 minutes natural coolings of heating reaction at 50-80 DEG C, add 0.495g chiralitys to 5-20 DEG C and lure
Reagent is led, is placed 20 hours, slowly crystallization filtering, obtains white crystal 18g, then recrystallize to obtain solid crystal 16g.
Solids 16g adds water 30g stirrings are lower to adjust PH7~8 with 10% ammonia spirit, cooling placement 5 hours at 10 DEG C
Filter to obtain white solid 4.5g yields 73%.
The of embodiment three
16.6g3- amino -3- phenylpropionic acids, 43.3g, chlorcamphor sulfonic acid are added in 250ml single port bottles and add water
16.6ml, ethanol 0.46ml, acetic acid 0.6ml, 30 minutes natural coolings of heating reaction at 50-80 DEG C, are cooled to 5-20 DEG C and add
Enter 0.433g chiral shift reagents, place 24 hours and slowly crystallize, filter to obtain white crystal, then 14.5g recrystallizes white
Solid crystal 13.3g.
Solids 13.3g adds lower 10% ammonia spirit regulation PH to the 7-8 coolings of water 30g stirrings, and it is small to place 10-15
When, filter to obtain white solid 4.3g yields 74.5%
Example IV：
The preparation of the amino -3- phenylpropionic acid camphorsulfonic acid double salt of S types optical isomer 3：
Amino -3- the phenylpropionic acids of racemic 3 are added in 250ml reaction bulbs：Water, acetic acid, ethanol, camphorsulfonic acid heating
50-80 DEG C is reacted 10 minutes, is cooled to 5-20 DEG C and is added chiral shift reagent placement crystallization, is filtrated to get S types optical isomer 3
Amino -3- phenylpropionic acid camphorsulfonic acid double salt.
The mol ratio of the chiral reagent and the racemic modification is 0.5~1.5:1.
The chiral shift reagent is camphorsulfonic acid neighbour's chlorobenzene sweet acid salt.
The chiral shift reagent is 0.001~0.005 with the racemic modification mol ratio：1.
Amino -3- phenylpropionic acid camphorsulfonic acids the double salt of S types optical isomer 3 is added, and uses mass concentration under agitation
It is 7-8 for 10% ammoniacal liquor regulation PH, cooling placement 5 hours, filter to obtain the amino -3- phenyl of S types optical isomer 3 at 10 DEG C
Propionic acid.
Embodiment five：
The preparation of the amino -3- phenylpropionic acid camphorsulfonic acid double salt of S types optical isomer 3：
Amino -3- the phenylpropionic acids of racemic 3 are added in 250ml reaction bulbs：Water, acetic acid, ethanol, camphorsulfonic acid heating
50-80 DEG C is reacted 30 minutes, is cooled to 5-20 DEG C and is added chiral shift reagent placement crystallization, is filtrated to get S types optical isomer 3
Amino -3- phenylpropionic acid camphorsulfonic acid double salt.
The mol ratio of the chiral reagent and the racemic modification is 0.5~1.5:1.
The chiral shift reagent is camphorsulfonic acid neighbour's chlorobenzene sweet acid salt.
The chiral shift reagent is 0.001~0.005 with the racemic modification mol ratio：1.
Amino -3- phenylpropionic acid camphorsulfonic acids the double salt of S types optical isomer 3 is added, and uses mass concentration under agitation
It is 7-8 for 10% ammoniacal liquor regulation PH, cooling placement 5 hours, filter to obtain the amino -3- phenyl of S types optical isomer 3 at 10 DEG C
Propionic acid.
Embodiment six：
The preparation of the amino -3- phenylpropionic acid camphorsulfonic acid double salt of R types optical isomer 3：
Amino -3- the phenylpropionic acids of racemic 3, water, acetic acid, ethanol, bromo-camphor sulfonic acid are added in 250ml reaction bulbs, is added
Warm 50-80 DEG C of reaction is cooled to 5-20 DEG C of addition chiral shift reagent placement for 10 minutes and is filtrated to get the ammonia of R types optical isomer 3
Base -3- phenylpropionic acid double salt.
The mol ratio of the chiral reagent and the racemic modification is 0.5~1.5:1.
The chiral shift reagent is bromo-camphor sulfonic acid hydroxyphenylglycine salt.
The chiral shift reagent is 0.001~0.005 with the racemic modification mol ratio：1.
Amino -3- phenylpropionic acid camphorsulfonic acids the double salt of R types optical isomer 3 is added, and uses mass concentration under agitation
It is 9-10 for 10% ammoniacal liquor regulation PH, filter liquor is adjusted back PH to 2-3 with the hydrochloric acid of mass concentration 10%, carried with dichloromethane
Take, dried without small magnesium sulfate, cooling is concentrated at 5-10 DEG C, is filtrated to get the R types optical isomer 3- amino -3- phenyl third
Acid.
Embodiment seven：
The preparation of the amino -3- phenylpropionic acid camphorsulfonic acid double salt of R types optical isomer 3：
Amino -3- the phenylpropionic acids of racemic 3, water, acetic acid, ethanol, bromo-camphor sulfonic acid are added in 250ml reaction bulbs, is added
Warm 50-80 DEG C of reaction is cooled to 5-20 DEG C of addition chiral shift reagent placement for 30 minutes and is filtrated to get the ammonia of R types optical isomer 3
Base -3- phenylpropionic acid double salt.
The mol ratio of the chiral reagent and the racemic modification is 0.5~1.5:1.
The chiral shift reagent is chlorcamphor sulfonic acid aminophenyl propionate.
The chiral shift reagent is 0.001~0.005 with the racemic modification mol ratio：1.
Amino -3- phenylpropionic acid camphorsulfonic acids the double salt of R types optical isomer 3 is added, and uses mass concentration under agitation
It is 9-10 for 10% ammoniacal liquor regulation PH, filter liquor is adjusted back PH to 2-3 with the hydrochloric acid of mass concentration 10%, carried with dichloromethane
Take, dried without small magnesium sulfate, cooling is concentrated at 5-10 DEG C, is filtrated to get the R types optical isomer 3- amino -3- phenyl third
Acid.
General principle, principal character and the advantages of the present invention of the present invention has been shown and described above.The technology of the industry
Personnel are it should be appreciated that the present invention is not limited to the above embodiments, and the simply explanation described in above-described embodiment and specification is originally
The principle of invention, without departing from the spirit and scope of the present invention, various changes and modifications of the present invention are possible, these changes
Change and improvement all fall within the protetion scope of the claimed invention.The claimed scope of the invention by appended claims and its
Equivalent thereof.
All all fall within the present invention's from the present invention is to devise, without the Structural Transformation made by creative work
Within protection domain.
Claims (6)
1. a kind of method for preparing S or R type optical isomer 3- amino -3- phenylpropionic acids, wherein R or S represent chiral centre structure
Type, it is characterised in that comprise the following steps：
1）The preparation of the amino -3- phenylpropionic acid camphorsulfonic acid double salt of S or R types optical isomer 3
Racemic modification 3- amino -3- phenylpropionic acids and chiral reagent are added in water, acetic acid, alcohol solvent and are warmed to 50-80
DEG C reaction 10-30 minutes, it is cooled to 5-20 DEG C afterwards, adds chiral shift reagent and place crystallization, be filtrated to get S or R type optics
Amino -3- phenylpropionic acid camphorsulfonic acid the double salt of isomers 3；The mol ratio of the chiral reagent and the racemic modification for 0.5~
1.5:1；The chiral shift reagent is 0.001~0.005 with the racemic modification mol ratio：1；
2）Free hydrolysis
Amino -3- phenylpropionic acid camphorsulfonic acid the double salt of S or R types optical isomer 3 is filtered after peracid or alkali free hydrolysis
To S the or R types optical isomer 3- amino -3- phenylpropionic acids.
2. the method as claimed in claim 1 for preparing S or R type optical isomer 3- amino -3- phenylpropionic acids, its feature exist
In：The chiral reagent includes optically active camphorsulfonic acid, bromo-camphor sulfonic acid, chlorcamphor sulfonic acid.
3. the method as claimed in claim 1 for preparing S or R type optical isomer 3- amino -3- phenylpropionic acids, its feature exist
In：The chiral shift reagent includes camphorsulfonic acid neighbour's chlorobenzene sweet acid salt, bromo-camphor sulfonic acid hydroxyphenylglycine salt, chlorcamphor
Sulfonic acid aminophenyl propionate.
4. the method as claimed in claim 1 for preparing S or R type optical isomer 3- amino -3- phenylpropionic acids, its feature exist
In：The step 2）In free hydrolysis include the amino -3- phenylpropionic acid camphorsulfonic acid double salt free waters of S types optical isomer 3
Solution and the amino -3- phenylpropionic acid camphorsulfonic acid double salt free hydrolysis of R types optical isomer 3.
5. the method as claimed in claim 4 for preparing S or R type optical isomer 3- amino -3- phenylpropionic acids, its feature exist
In：Amino -3- phenylpropionic acid camphorsulfonic acid double salt the free hydrolysis of S types optical isomer 3 is by the ammonia of S types optical isomer 3
Base -3- phenylpropionic acid camphorsulfonic acids double salt adds, and the ammoniacal liquor regulation PH for being under agitation 10% with mass concentration is 7-8,10
Cooling is placed 5 hours at DEG C, filters to obtain the amino -3- phenylpropionic acids of S types optical isomer 3.
6. the method as claimed in claim 4 for preparing S or R type optical isomer 3- amino -3- phenylpropionic acids, its feature exist
In：Amino -3- phenylpropionic acid camphorsulfonic acid double salt the free hydrolysis of R types optical isomer 3 is by the ammonia of R types optical isomer 3
Base -3- phenylpropionic acid camphorsulfonic acids double salt adds, and the ammoniacal liquor regulation PH for being under agitation 10% with mass concentration is 9-10, mistake
Filter filtrate and adjust back PH to 2-3 with the hydrochloric acid of mass concentration 10%, extracted with dichloromethane, anhydrous magnesium sulfate is dried, dense at 5-10 DEG C
Contracting cooling, is filtrated to get the R types optical isomer 3- amino -3- phenylpropionic acids.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1331072A (en) * | 2000-07-05 | 2002-01-16 | 北京清华紫光英力化工技术有限责任公司 | Process for prearing R-(t)-N-(substituted phenyl) lactamic acid or its ester |
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2014
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1331072A (en) * | 2000-07-05 | 2002-01-16 | 北京清华紫光英力化工技术有限责任公司 | Process for prearing R-(t)-N-(substituted phenyl) lactamic acid or its ester |
Non-Patent Citations (3)
| Title |
|---|
| "D-色氨酸的制备工艺研究";彭加平 等;《药物生物技术》;20131231;第20卷(第6期);541-544 * |
| "β-氨基酸的合成与手性拆分";陈峰;《中国优秀硕士学位论文全文数据库工程科技Ⅰ辑》;20090415;B016-331 * |
| "手性氨基酸对映体的拆分";方岩雄 等;《广东工业大学学报》;20020930;第19卷(第3期);第7-10页 * |
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