CN106674030A - Preparation method of N-fluorenylmethyloxycarbonyl-L-2-amino-4-cyclohexylbutyric acid - Google Patents
Preparation method of N-fluorenylmethyloxycarbonyl-L-2-amino-4-cyclohexylbutyric acid Download PDFInfo
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- CN106674030A CN106674030A CN201611180892.3A CN201611180892A CN106674030A CN 106674030 A CN106674030 A CN 106674030A CN 201611180892 A CN201611180892 A CN 201611180892A CN 106674030 A CN106674030 A CN 106674030A
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- Prior art keywords
- amino
- fluorenylmethyloxycarbonyl
- butyric acids
- cyclohexyl
- cyclohexyl butyric
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/16—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions not involving the amino or carboxyl groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/04—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups from amines with formation of carbamate groups
Abstract
The invention discloses a preparation method of N-fluorenylmethyloxycarbonyl-L-2-amino-4-cyclohexylbutyric acid. The method comprises the following steps: A: L-2-amino-4-phenylbutyric acid is dissolved in alkaline water, a platinum carbon catalyst is added, hydrogen is introduced for 8-12 hours, after the reaction ends, clarified transparent filtrate is collected, after acidifying, filtering, washing and drying are carried out in order to obtain L-2-amino-4-cyclohexylbutyric acid; B: L-2-amino-4-cyclohexylbutyric acid obtained in the step A is dissolved in alkaline water, N-(9-fluorenylmethoxycarbonyloxy)succinimide is added, stirring is carried out, acetone is added equivalently for three times, after the reaction ends, filtrate is acidified with 6mol/L hydrochloric acid, extraction is carried out with ethyl acetate, petroleum ether is added for crystallization, filtering and drying are carried out in order to obtain an target product N-fluorenylmethyloxycarbonyl-L-2-amino-4-cyclohexylbutyric acid. Compared with the prior art, reaction time is substantially shortened, reaction temperature and reaction pressure are reduced, the whole reaction is beneficial for control, accident rate is reduced, product purity is higher than 99.5%, and yield exceeds 87%.
Description
Technical field
Present invention relates particularly to a kind of preparation method of N- fluorenylmethyloxycarbonyls-L-2- amino -4- cyclohexyl butyric acids.
Background technology
The structural formula of N- fluorenylmethyloxycarbonyl-L-2- amino -4- cyclohexyl butyric acids is as follows：
N- fluorenylmethyloxycarbonyl-L-2- amino -4- cyclohexyl butyric acids are a kind of useful organic intermediates, in emerging medicine and polypeptide
Study on the synthesis on have application, the industrial process of scale is there is no at present.The country does not synthesize the report of the compound also
Road.
Similar compound traditional handicraft is comprised the following steps that：A is dissolved in alkali with L-2- amino-4-phenyl butyric acid as raw material
Carry out hydrogenating under water, plus ruthenium catalyst, HTHP and obtain L-2- amino -4- cyclohexyl butyric acids；（2）L-2- amino -4- hexamethylenes
Base butyric acid is dissolved in alkali, chloro-carbonic acid -9- fluorenyl methyl esters is added dropwise at 0 DEG C, it is ensured that below 5 DEG C of system temperature, be added dropwise to complete rear normal temperature anti-
Answer 24 hours, ethyl acetate extraction after acidifying, concentrate ethyl acetate layer, plus petroleum ether crystallization, filtering, drying obtains N- fluorenes methoxies
Carbonyl-L-2- amino -4- cyclohexyl butyric acids.
Traditional handicraft, hydrogenated fractions reaction temperature is high, and pressure is big, hardly possible control, danger increase；Amido protecting part, instead
The control requirement for tackling temperature is higher, and reaction is slow, and accessory substance is more, and is unfavorable for that the later stage amplifies production, in addition, conventional method
Yield less than 85%, yield is relatively low.
The content of the invention
For deficiency of the prior art, the present invention provides a kind of N- fluorenylmethyloxycarbonyls-L-2- amino -4- cyclohexyl butyric acids
Preparation method.
A kind of preparation method of N- fluorenylmethyloxycarbonyls-L-2- amino -4- cyclohexyl butyric acids, comprises the following steps：
A:Raw material L-2- amino-4-phenyl butyric acid is dissolved in buck, is then added in stainless steel autoclave, added in kettle
Enter platinum carbon catalyst, be passed through hydrogen 8-12 hours, 20-60 DEG C of temperature in the kettle, reacted under pressure 1.0-2.5MPa；After reaction terminates
Autoclave is vented, blowing, and clear filtrate is collected after resulting material filtering, and filtrate is acidified with 6mol/L hydrochloric acid, regulation system
PH to 6.0-7.0, after acidifying, filtering, washing, drying obtains L-2- amino -4- cyclohexyl butyric acids；
B:L-2- amino -4- cyclohexyl butyric acids obtained by step A are dissolved in buck, 9- fluorene methyl-N- succinyls are added
Iminocarbonates, stirring, then equivalent adds acetone in three times, and per minor tick half an hour, normal-temperature reaction 3-5 hours, reaction knot
Filtrate is acidified with 6mol/L hydrochloric acid after beam, regulation system PH to 6.0-7.0, ethyl acetate extraction, is added after ethyl acetate layer concentration
Petroleum ether is crystallized, and filtering drying obtains target product N- fluorenylmethyloxycarbonyl-L-2- amino -4- cyclohexyl butyric acids.
Preferably：Buck described in step A is potassium hydroxide or sodium hydroxide solution, and described buck concentration is
0.75-1.0mol/L。
Further：Raw material L-2- amino-4-phenyls butyric acid and the consumption proportion of the aqueous alkali are every 1 gram in step A
L-2- amino-4-phenyls butyric acid uses aqueous alkali 4ml-15ml.
Preferably：Platinum catalyst described in step A is the charcoal platinum catalyst of platinum content 5.0%-20.0%.
Preferably：It is 0.02-0.06 according to the platinum catalyst described in mass ratio and L-2- amino-4-phenyls butyric acid proportioning:
1。
Preferably：Buck described in step B is sodium carbonate or sodium bicarbonate solution, and its concentration is 1.0-3.0mol/
L。
Further：L-2- amino-4-phenyls butyric acid and the proportioning of aqueous alkali described in step B are every 1 gram of L-2- ammonia
Base -4-phenylbutyrate uses aqueous alkali 8ml-12ml.
Preferably：9- fluorene methyls-N- succinimidyl carbonates described in step B and L-2- amino -4- cyclohexyl fourths
The proportioning of acid is according to mass ratio 1.9-2.0：1.
Preferably：The proportioning of acetone and L-2- amino -4- cyclohexyl butyric acids is according to mass ratio 3-4 in step B:1.
The invention provides a kind of preparation method of N- fluorenylmethyloxycarbonyls-L-2- amino -4- cyclohexyl butyric acids, relative to existing
There is technology, substantially reduce the reaction time, reduce reaction temperature and reaction pressure, make whole reaction beneficial to control, reduce thing
Therefore incidence, more than 99.5%, yield is more than 87% for obtained product purity.
Specific embodiment
In below in conjunction with the embodiment of the present invention, the technical scheme in the embodiment of the present invention is clearly and completely retouched
State.
Embodiment 1：A kind of preparation method of N- fluorenylmethyloxycarbonyls-L-2- amino -4- cyclohexyl butyric acids, including following step
Suddenly：
A:10kg raw material L-2- amino-4-phenyl butyric acid is dissolved in 100L（40-150）Concentration is 0.8mol/L（0.75-1）'s
In sodium hydroxide solution, it is then added in stainless steel autoclave, to addition platinum content 10% in kettle（5-20）Charcoal platinum carried catalysis
Agent 0.4（0.2-0.58）Kg, is passed through hydrogen 9（8-12）Hour, 45 DEG C of temperature in the kettle（20-60）, pressure 1.7（1-2.5）Under MPa
Reaction；Reaction terminates rear autoclave emptying, and blowing collects clear filtrate after resulting material filtering, and filtrate uses 6mol/L salt
Acid acidifying, between regulation system PH to 6.0-7.0, after acidifying, filtering, washing, drying obtains L-2- amino -4- cyclohexyl fourths
Acid；
B:L-2- amino -4- cyclohexyl butyric acids obtained by step A are dissolved in concentration for 2mol/L（1.0-3. 0）Sodium carbonate
In solution, 20kg9- fluorene methyl-N- succinimidyl carbonates, stirring are added, then equivalent adds the common 35kg of acetone in three times
（30-40）, per minor tick half an hour, normal-temperature reaction 4 hours, reaction terminates rear filtrate and is acidified with 6mol/L hydrochloric acid, regulation system
PH to 6.0-7.0, ethyl acetate extraction adds petroleum ether crystallization after ethyl acetate layer concentration, filtering drying obtains target product N- fluorenes
Methoxycarbonyl group-L-2- amino -4- cyclohexyl butyric acids.By weighing and analyzing, the yield of target product position 91.0%, purity is
99.87%。
Embodiment 2：A kind of preparation method of N- fluorenylmethyloxycarbonyls-L-2- amino -4- cyclohexyl butyric acids, including following step
Suddenly：
A:10kg raw material L-2- amino-4-phenyl butyric acid is dissolved in the potassium hydroxide solution that 50L concentration is 0.9mol/L, so
After be added in stainless steel autoclave, in kettle add platinum content 10% charcoal platinum catalyst 0.4）Kg, is passed through hydrogen 9 hours,
45 DEG C of temperature in the kettle, reacts under pressure 1.7MPa；Reaction terminates rear autoclave emptying, and blowing collects clear after resulting material filtering
Clear clear filtrate, filtrate is acidified with 6mol/L hydrochloric acid, between regulation system PH to 6.0-7.0, after acidifying, filtering, washing, drying
Obtain L-2- amino -4- cyclohexyl butyric acids；
B:L-2- amino -4- cyclohexyl butyric acids obtained by step A are dissolved in concentration in 2mol/L sodium bicarbonate solutions, plus
Enter 20kg9- fluorene methyl-N- succinimidyl carbonates, stir, then equivalent adds the common 35kg of acetone in three times, per minor tick
Half an hour, normal-temperature reaction 4 hours, reaction terminates rear filtrate and is acidified with 6mol/L hydrochloric acid, regulation system PH to 6.0-7.0, acetic acid
Ethyl ester is extracted, and petroleum ether crystallization is added after ethyl acetate layer concentration, and filtering drying obtains target product N- fluorenylmethyloxycarbonyl-L-2- ammonia
Base -4- cyclohexyl butyric acids.By weighing and analyzing, the yield position 90.5% of target product, purity is 99.76%.
Embodiment 3：A kind of preparation method of N- fluorenylmethyloxycarbonyls-L-2- amino -4- cyclohexyl butyric acids, including following step
Suddenly：
A:10kg raw material L-2- amino-4-phenyl butyric acid is dissolved in the sodium hydroxide solution that 135L concentration is 0.8mol/L,
It is then added in stainless steel autoclave, to the charcoal platinum catalyst 0.25kg that platinum content 17% is added in kettle, is passed through hydrogen 9 small
When, 33 DEG C of temperature in the kettle reacts under pressure 1.4MPa；Reaction terminates rear autoclave emptying, and blowing is collected after resulting material filtering
Clear filtrate, filtrate is acidified with 6mol/L hydrochloric acid, and between regulation system PH to 6.0-7.0, after acidifying, filtering, washing is dried
It is dry to obtain L-2- amino -4- cyclohexyl butyric acids；
B:L-2- amino -4- cyclohexyl butyric acids obtained by step A are dissolved in concentration in 2mol/L sodium carbonate liquors, to add
20kg9- fluorene methyl-N- succinimidyl carbonates, stirring, then equivalent adds the common 35kg of acetone in three times, half per minor tick
Hour, normal-temperature reaction 4 hours, reaction terminates rear filtrate and is acidified with 6mol/L hydrochloric acid, regulation system PH to 6.0-7.0, acetic acid second
Ester extract, ethyl acetate layer concentration after plus petroleum ether crystallization, filtering drying obtain target product N- fluorenylmethyloxycarbonyl-L-2- amino-
4- cyclohexyl butyric acids.By weighing and analyzing, the yield position 89.3% of target product, purity is 99.45%.
Embodiment 4：A kind of preparation method of N- fluorenylmethyloxycarbonyls-L-2- amino -4- cyclohexyl butyric acids, including following step
Suddenly：
A:10kg raw material L-2- amino-4-phenyl butyric acid is dissolved in the sodium hydroxide solution that 100L concentration is 1.0mol/L,
It is then added in stainless steel autoclave, to the charcoal platinum catalyst 0.4kg that platinum content 6% is added in kettle, is passed through hydrogen 11 small
When, 55 DEG C of temperature in the kettle reacts under pressure 1.7MPa；Reaction terminates rear autoclave emptying, and blowing is collected after resulting material filtering
Clear filtrate, filtrate is acidified with 6mol/L hydrochloric acid, and between regulation system PH to 6.0-7.0, after acidifying, filtering, washing is dried
It is dry to obtain L-2- amino -4- cyclohexyl butyric acids；
B:L-2- amino -4- cyclohexyl butyric acids obtained by step A are dissolved in concentration in 2mol/L sodium carbonate liquors, to add
20kg9- fluorene methyl-N- succinimidyl carbonates, stirring, then equivalent adds the common 35kg of acetone in three times, half per minor tick
Hour, normal-temperature reaction 4 hours, reaction terminates rear filtrate and is acidified with 6mol/L hydrochloric acid, regulation system PH to 6.0-7.0, acetic acid second
Ester extract, ethyl acetate layer concentration after plus petroleum ether crystallization, filtering drying obtain target product N- fluorenylmethyloxycarbonyl-L-2- amino-
4- cyclohexyl butyric acids.By weighing and analyzing, the yield position 88.44% of target product, purity is 99.82%.
Embodiment five：A kind of preparation method of N- fluorenylmethyloxycarbonyls-L-2- amino -4- cyclohexyl butyric acids, including following step
Suddenly：
A:10kg raw material L-2- amino-4-phenyl butyric acid is dissolved in the potassium hydroxide solution that 100L concentration is 0.8mol/L,
It is then added in stainless steel autoclave, to the charcoal platinum catalyst 0.53kg that platinum content 7% is added in kettle, is passed through hydrogen 10 small
When, 45 DEG C of temperature in the kettle, pressure 1.2）Reacted under MPa；Reaction terminates rear autoclave emptying, and blowing is received after resulting material filtering
Collection clear filtrate, filtrate is acidified with 6mol/L hydrochloric acid, between regulation system PH to 6.0-7.0, after acidifying, filtering, washing,
Drying obtains L-2- amino -4- cyclohexyl butyric acids；
B:L-2- amino -4- cyclohexyl butyric acids obtained by step A are dissolved in concentration in 2mol/L sodium carbonate liquors, to add
20kg9- fluorene methyl-N- succinimidyl carbonates, stirring, then equivalent adds the common 31kg of acetone in three times, half per minor tick
Hour, normal-temperature reaction 4 hours, reaction terminates rear filtrate and is acidified with 6mol/L hydrochloric acid, regulation system PH to 6.0-7.0, acetic acid second
Ester extract, ethyl acetate layer concentration after plus petroleum ether crystallization, filtering drying obtain target product N- fluorenylmethyloxycarbonyl-L-2- amino-
4- cyclohexyl butyric acids.By weighing and analyzing, the yield position 92.0% of target product, purity is 99.11%.
Embodiment six：A kind of preparation method of N- fluorenylmethyloxycarbonyls-L-2- amino -4- cyclohexyl butyric acids, including following step
Suddenly：
A:10kg raw material L-2- amino-4-phenyl butyric acid is dissolved in the sodium hydroxide solution that 135L concentration is 0.8mol/L,
It is then added in stainless steel autoclave, to the charcoal platinum catalyst 0.55kg that platinum content 10% is added in kettle, is passed through hydrogen 11 small
When, 55 DEG C of temperature in the kettle reacts under pressure 2.3MPa；Reaction terminates rear autoclave emptying, and blowing is collected after resulting material filtering
Clear filtrate, filtrate is acidified with 6mol/L hydrochloric acid, and between regulation system PH to 6.0-7.0, after acidifying, filtering, washing is dried
It is dry to obtain L-2- amino -4- cyclohexyl butyric acids；
B:L-2- amino -4- cyclohexyl butyric acids obtained by step A are dissolved in concentration in 2mol/L sodium carbonate liquors, to add
20kg9- fluorene methyl-N- succinimidyl carbonates, stirring, then equivalent adds the common 35kg of acetone in three times, half per minor tick
Hour, normal-temperature reaction 4 hours, reaction terminates rear filtrate and is acidified with 6mol/L hydrochloric acid, regulation system PH to 6.0-7.0, acetic acid second
Ester extract, ethyl acetate layer concentration after plus petroleum ether crystallization, filtering drying obtain target product N- fluorenylmethyloxycarbonyl-L-2- amino-
4- cyclohexyl butyric acids.By weighing and analyzing, the yield position 92.23% of target product, purity is 99.17%.
Embodiment seven：A kind of preparation method of N- fluorenylmethyloxycarbonyls-L-2- amino -4- cyclohexyl butyric acids, including following step
Suddenly：
A:10kg raw material L-2- amino-4-phenyl butyric acid is dissolved in the sodium hydroxide solution that 100L concentration is 0.9mol/L,
It is then added in stainless steel autoclave, to the charcoal platinum catalyst 0.4kg that platinum content 15% is added in kettle, is passed through hydrogen 8 small
When, 35 DEG C of temperature in the kettle reacts under pressure 1.4MPa；Reaction terminates rear autoclave emptying, and blowing is collected after resulting material filtering
Clear filtrate, filtrate is acidified with 6mol/L hydrochloric acid, and between regulation system PH to 6.0-7.0, after acidifying, filtering, washing is dried
It is dry to obtain L-2- amino -4- cyclohexyl butyric acids；
B:L-2- amino -4- cyclohexyl butyric acids obtained by step A are dissolved in concentration in 2mol/L sodium carbonate liquors, to add
20kg9- fluorene methyl-N- succinimidyl carbonates, stirring, then equivalent adds the common 35kg of acetone in three times, half per minor tick
Hour, normal-temperature reaction 3-5 hours, reaction terminated rear filtrate and is acidified with 6mol/L hydrochloric acid, regulation system PH to 6.0-7.0, acetic acid
Ethyl ester is extracted, and petroleum ether crystallization is added after ethyl acetate layer concentration, and filtering drying obtains target product N- fluorenylmethyloxycarbonyl-L-2- ammonia
Base -4- cyclohexyl butyric acids.By weighing and analyzing, the yield position 91.56% of target product, purity is 99.74%.
Various modifications to these embodiments will be apparent for those skilled in the art, herein
Defined General Principle can be realized in other embodiments without departing from the spirit or scope of the present invention.
Claims (9)
1. a kind of preparation method of N- fluorenylmethyloxycarbonyls-L-2- amino -4- cyclohexyl butyric acids, it is characterised in that including following step
Suddenly：
A:Raw material L-2- amino-4-phenyl butyric acid is dissolved in buck, is then added in stainless steel autoclave, added in kettle
Enter platinum carbon catalyst, be passed through hydrogen 8-12 hours, 20-60 DEG C of temperature in the kettle, reacted under pressure 1.0-2.5MPa；After reaction terminates
Autoclave is vented, blowing, and clear filtrate is collected after resulting material filtering, and filtrate is acidified with 6mol/L hydrochloric acid, regulation system
PH to 6.0-7.0, after acidifying, filtering, washing, drying obtains L-2- amino -4- cyclohexyl butyric acids；
B:L-2- amino -4- cyclohexyl butyric acids obtained by step A are dissolved in buck, 9- fluorene methyl-N- succinyls are added
Iminocarbonates, stirring, then equivalent adds acetone in three times, and per minor tick half an hour, normal-temperature reaction 3-5 hours, reaction knot
Filtrate is acidified with 6mol/L hydrochloric acid after beam, regulation system PH to 6.0-7.0, ethyl acetate extraction, is added after ethyl acetate layer concentration
Petroleum ether is crystallized, and filtering drying obtains target product N- fluorenylmethyloxycarbonyl-L-2- amino -4- cyclohexyl butyric acids.
2. the method for preparing N- fluorenylmethyloxycarbonyl-L-2- amino -4- cyclohexyl butyric acids according to claim 1, its feature
It is：Buck described in step A is potassium hydroxide or sodium hydroxide solution, and described buck concentration is 0.75-1.0mol/L.
3. the method for preparing N- fluorenylmethyloxycarbonyl-L-2- amino -4- cyclohexyl butyric acids according to claim 1 and 2, it is special
Levy and be：In step A raw material L-2- amino-4-phenyls butyric acid and the consumption proportion of the aqueous alkali be every 1 gram of L-2- amino-
4-phenylbutyrate uses aqueous alkali 4ml-15ml.
4. the method for preparing N- fluorenylmethyloxycarbonyl-L-2- amino -4- cyclohexyl butyric acids according to claim 1, its feature
It is：Platinum catalyst described in step A is the charcoal platinum catalyst of platinum content 5.0%-20.0%.
5. the method for preparing N- fluorenylmethyloxycarbonyl-L-2- amino -4- cyclohexyl butyric acids according to claim 4, its feature
It is：It is 0.02-0.06 according to the platinum catalyst described in mass ratio and L-2- amino-4-phenyls butyric acid proportioning:1.
6. the method for preparing N- fluorenylmethyloxycarbonyl-L-2- amino -4- cyclohexyl butyric acids according to claim 1, its feature
It is：Buck described in step B is sodium carbonate or sodium bicarbonate solution, and its concentration is 1.0-3.0mol/L.
7. the method for preparing N- fluorenylmethyloxycarbonyl-L-2- amino -4- cyclohexyl butyric acids according to claim 6, its feature
It is：L-2- amino-4-phenyls butyric acid and the proportioning of aqueous alkali described in step B are every 1 gram of L-2- amino-4-phenyl fourths
Acid uses aqueous alkali 8ml-12ml.
8. the method for preparing N- fluorenylmethyloxycarbonyl-L-2- amino -4- cyclohexyl butyric acids according to claim 1, its feature
It is：The proportioning of 9- fluorene methyls-N- succinimidyl carbonates described in step B and L-2- amino -4- cyclohexyl butyric acids is
According to mass ratio 1.9-2.0：1.
9. the method for preparing N- fluorenylmethyloxycarbonyl-L-2- amino -4- cyclohexyl butyric acids according to claim 1, its feature
It is：The proportioning of acetone and L-2- amino -4- cyclohexyl butyric acids is according to mass ratio 3-4 in step B:1.
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| CN110256310A (en) * | 2019-07-01 | 2019-09-20 | 吉尔生化（上海）有限公司 | A kind of preparation method of N- fluorenylmethyloxycarbonyl-S- (4- Methoxytrityl)-L- homocysteine |
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Application publication date: 20170517 |