CN110143896A - A kind of preparation method of N- benzyloxycarbonyl group-L- glycoleucine - Google Patents
A kind of preparation method of N- benzyloxycarbonyl group-L- glycoleucine Download PDFInfo
- Publication number
- CN110143896A CN110143896A CN201910516874.5A CN201910516874A CN110143896A CN 110143896 A CN110143896 A CN 110143896A CN 201910516874 A CN201910516874 A CN 201910516874A CN 110143896 A CN110143896 A CN 110143896A
- Authority
- CN
- China
- Prior art keywords
- glycoleucine
- benzyloxycarbonyl group
- preparation
- centrifuge
- solution
- 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.)
- Pending
Links
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of preparation methods of N- benzyloxycarbonyl group-L- glycoleucine, belong to medicine intermediate field comprising L- glycoleucine, alkali are added in organic solvent by following steps, and the weight of organic solvent is 6~8 times of L- glycoleucine weight；Benzyl chloroformate is added dropwise in the solution of S1, separates the water that reaction generates with water segregator, is cooled to 10~15 DEG C, obtains N- benzyloxycarbonyl group-L- glycoleucine feed liquid；Further purification: N- benzyloxycarbonyl group-L- glycoleucine feed liquid is put into a centrifuge, the revolving speed for adjusting centrifuge is 10000~12000r/min, it is then centrifuged for 2~4min, the centrifugal liquid being divided into, the supernatant of centrifugal liquid is discharged, N- benzyloxycarbonyl group-L- glycoleucine the solution for retaining part, as needs N- benzyloxycarbonyl group-L- glycoleucine to be prepared.Present invention process is simple, at low cost, and obtained product purity is high, is suitble to promote the use of.
Description
Technical field
The present invention relates to medicine intermediate technical field more particularly to a kind of preparation sides of N- benzyloxycarbonyl group-L- glycoleucine
Method.
Background technique
So-called medicine intermediate, more actually for some industrial chemicals or chemical industry in drug synthesis process
Product.This chemical products do not need the production licence of drug, can produce in common chemical plant, as long as reaching
Rank, can be used to the synthesis of drug.
N- benzyloxycarbonyl group-L- glycoleucine is relatively common medicine intermediate, is applied in medicine synthesis, existing N- benzyl
Oxygen carbonyl-L- glycoleucine synthesis technology is relatively complicated, and at high cost, purity is not high, for this purpose, the present invention proposes a kind of N- benzyloxy carbonyl
The preparation method of base-L- glycoleucine.
Summary of the invention
The purpose of the present invention is to solve disadvantages existing in the prior art, and a kind of N- benzyloxycarbonyl group-L- proposed
The preparation method of glycoleucine.
To achieve the goals above, present invention employs following technical solutions:
A kind of preparation method of N- benzyloxycarbonyl group-L- glycoleucine, includes the following steps,
L- glycoleucine, alkali are added in organic solvent by S1, and the weight of organic solvent is 6~8 times of L- glycoleucine weight；
Benzyl chloroformate is added dropwise in the solution of S1 in S2, reacts 2.5~4.5 hours at 25~35 DEG C after dripping off, reaction terminates
After be heated to flowing back, with water segregator separate reaction generate water, be cooled to 10~15 DEG C, obtain N- benzyloxycarbonyl group-L- glycoleucine
Feed liquid；
S3 is further purified: N- benzyloxycarbonyl group-L- glycoleucine feed liquid being put into a centrifuge, the revolving speed for adjusting centrifuge is
10000~12000r/min is then centrifuged for 2~4min, the centrifugal liquid being divided into, and the supernatant of centrifugal liquid is discharged,
N- benzyloxycarbonyl group-L- glycoleucine the solution for retaining part, as needs N- benzyloxycarbonyl group-L- glycoleucine to be prepared.
Preferably, the alkali is one of sodium bicarbonate, sodium carbonate and potassium carbonate or a variety of mixtures.
Preferably, the organic solvent uses toluene.
Preferably, in the S2, benzyl chloroformate is added dropwise in the solution of S1, is reacted 3.2 hours at 30 DEG C after dripping off,
Be heated to flowing back after reaction, with water segregator separate reaction generate water, be cooled to 12 DEG C, obtain N- benzyloxycarbonyl group-L- oneself
Propylhomoserin feed liquid.
Preferably, it in the S3, further purifies: N- benzyloxycarbonyl group-L- glycoleucine feed liquid is put into a centrifuge, adjust
The revolving speed of centrifuge is 11000r/min, is then centrifuged for 3min, the centrifugal liquid being divided into, and the supernatant of centrifugal liquid is arranged
Out, the N- benzyloxycarbonyl group-L- glycoleucine solution for retaining part, as needs N- benzyloxycarbonyl group-L- glycoleucine to be prepared.
Compared with prior art, the beneficial effects of the present invention are: by the way that L- glycoleucine, alkali are added in organic solvent,
The weight of organic solvent is 6~8 times of L- glycoleucine weight, in alkaline environment, can react more quickly, sufficiently, obtain
The purity of product is higher, and the revolving speed by adjusting centrifuge is 10000~12000r/min, is then centrifuged for 2~4min, further
The purity for improving product can achieve 99% purity, and simple process and low cost of the invention, obtained product purity is high, fits
It closes and promotes the use of.
Specific embodiment
The technical scheme in the embodiments of the invention will be clearly and completely described below, it is clear that described implementation
Example is only a part of the embodiment of the present invention, instead of all the embodiments.
Embodiment one
A kind of preparation method of N- benzyloxycarbonyl group-L- glycoleucine proposed by the present invention, includes the following steps,
L- glycoleucine, alkali are added in organic solvent by S1, and the weight of organic solvent is 6 times of L- glycoleucine weight；
Benzyl chloroformate is added dropwise in the solution of S1 in S2, reacts 2.5 hours at 25 DEG C after dripping off, is heated to after reaction
Reflux separates the water that reaction generates with water segregator, is cooled to 10 DEG C, obtains N- benzyloxycarbonyl group-L- glycoleucine feed liquid；
S3 is further purified: N- benzyloxycarbonyl group-L- glycoleucine feed liquid being put into a centrifuge, the revolving speed for adjusting centrifuge is
10000r/min is then centrifuged for 2min, the centrifugal liquid being divided into, and the supernatant of centrifugal liquid is discharged, part is retained
N- benzyloxycarbonyl group-L- glycoleucine solution, as need N- benzyloxycarbonyl group-L- glycoleucine to be prepared.
Embodiment two
A kind of preparation method of N- benzyloxycarbonyl group-L- glycoleucine proposed by the present invention, includes the following steps,
L- glycoleucine, alkali are added in organic solvent by S1, and the weight of organic solvent is 7 times of L- glycoleucine weight；
Benzyl chloroformate is added dropwise in the solution of S1 in S2, reacts 3.2 hours at 30 DEG C after dripping off, is heated to after reaction
Reflux separates the water that reaction generates with water segregator, is cooled to 12 DEG C, obtains N- benzyloxycarbonyl group-L- glycoleucine feed liquid；
S3 is further purified: N- benzyloxycarbonyl group-L- glycoleucine feed liquid being put into a centrifuge, the revolving speed for adjusting centrifuge is
11000r/min is then centrifuged for 3min, the centrifugal liquid being divided into, and the supernatant of centrifugal liquid is discharged, part is retained
N- benzyloxycarbonyl group-L- glycoleucine solution, as need N- benzyloxycarbonyl group-L- glycoleucine to be prepared.
Embodiment three
A kind of preparation method of N- benzyloxycarbonyl group-L- glycoleucine proposed by the present invention, includes the following steps,
L- glycoleucine, alkali are added in organic solvent by S1, and the weight of organic solvent is 8 times of L- glycoleucine weight；
Benzyl chloroformate is added dropwise in the solution of S1 in S2, reacts 4.5 hours at 35 DEG C after dripping off, is heated to after reaction
Reflux separates the water that reaction generates with water segregator, is cooled to 15 DEG C, obtains N- benzyloxycarbonyl group-L- glycoleucine feed liquid；
S3 is further purified: N- benzyloxycarbonyl group-L- glycoleucine feed liquid being put into a centrifuge, the revolving speed for adjusting centrifuge is
12000r/min is then centrifuged for 4min, the centrifugal liquid being divided into, and the supernatant of centrifugal liquid is discharged, part is retained
N- benzyloxycarbonyl group-L- glycoleucine solution, as need N- benzyloxycarbonyl group-L- glycoleucine to be prepared.
In the present invention, by the way that L- glycoleucine, alkali to be added in organic solvent, the weight of organic solvent is L- glycoleucine weight
6~8 times of amount can react more quickly, sufficiently in alkaline environment, and the purity for obtaining product is higher, is centrifuged by adjusting
The revolving speed of machine is 10000~12000r/min, is then centrifuged for 2~4min, further increases the purity of product, can achieve 99%
Purity, simple process and low cost of the invention, obtained product purity is high, is suitble to promote the use of.
The foregoing is only a preferred embodiment of the present invention, but scope of protection of the present invention is not limited thereto,
Anyone skilled in the art in the technical scope disclosed by the present invention, according to the technique and scheme of the present invention and its
Inventive concept is subject to equivalent substitution or change, should be covered by the protection scope of the present invention.
Claims (5)
1. a kind of preparation method of N- benzyloxycarbonyl group-L- glycoleucine, which is characterized in that include the following steps,
L- glycoleucine, alkali are added in organic solvent by S1, and the weight of organic solvent is 6~8 times of L- glycoleucine weight；
Benzyl chloroformate is added dropwise in the solution of S1 in S2, reacts 2.5~4.5 hours at 25~35 DEG C after dripping off, reaction terminates
After be heated to flowing back, with water segregator separate reaction generate water, be cooled to 10~15 DEG C, obtain N- benzyloxycarbonyl group-L- glycoleucine
Feed liquid；
S3 is further purified: N- benzyloxycarbonyl group-L- glycoleucine feed liquid being put into a centrifuge, the revolving speed for adjusting centrifuge is
10000~12000r/min is then centrifuged for 2~4min, the centrifugal liquid being divided into, and the supernatant of centrifugal liquid is discharged,
N- benzyloxycarbonyl group-L- glycoleucine the solution for retaining part, as needs N- benzyloxycarbonyl group-L- glycoleucine to be prepared.
2. a kind of preparation method of N- benzyloxycarbonyl group-L- glycoleucine according to claim 1, which is characterized in that the alkali
For one of sodium bicarbonate, sodium carbonate and potassium carbonate or a variety of mixtures.
3. a kind of preparation method of N- benzyloxycarbonyl group-L- glycoleucine according to claim 1, which is characterized in that described to have
Solvent uses toluene.
4. a kind of preparation method of N- benzyloxycarbonyl group-L- glycoleucine according to claim 1, which is characterized in that the S2
In, benzyl chloroformate is added dropwise in the solution of S1, is reacted 3.2 hours at 30 DEG C after dripping off, is heated to flowing back after reaction,
The water that reaction generates is separated with water segregator, 12 DEG C is cooled to, obtains N- benzyloxycarbonyl group-L- glycoleucine feed liquid.
5. a kind of preparation method of N- benzyloxycarbonyl group-L- glycoleucine according to claim 1, which is characterized in that the S3
In, it further purifies: N- benzyloxycarbonyl group-L- glycoleucine feed liquid is put into a centrifuge, the revolving speed for adjusting centrifuge is 11000r/
Min is then centrifuged for 3min, the centrifugal liquid being divided into, and the supernatant of centrifugal liquid is discharged, the N- benzyloxy of part is retained
Carbonyl-L- glycoleucine solution as needs N- benzyloxycarbonyl group-L- glycoleucine to be prepared.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910516874.5A CN110143896A (en) | 2019-06-14 | 2019-06-14 | A kind of preparation method of N- benzyloxycarbonyl group-L- glycoleucine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910516874.5A CN110143896A (en) | 2019-06-14 | 2019-06-14 | A kind of preparation method of N- benzyloxycarbonyl group-L- glycoleucine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN110143896A true CN110143896A (en) | 2019-08-20 |
Family
ID=67591390
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910516874.5A Pending CN110143896A (en) | 2019-06-14 | 2019-06-14 | A kind of preparation method of N- benzyloxycarbonyl group-L- glycoleucine |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN110143896A (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5492921A (en) * | 1977-12-20 | 1979-07-23 | Hoffmann La Roche | Peptide derivative |
| CN103204905A (en) * | 2013-03-15 | 2013-07-17 | 四川同晟生物科技有限公司 | Method for synthesizing tetra-glycylglycine |
| CN104086475A (en) * | 2014-07-15 | 2014-10-08 | 苏州天马精细化学品股份有限公司 | Preparation method of N-carbobenzoxy-L-prolinamide |
-
2019
- 2019-06-14 CN CN201910516874.5A patent/CN110143896A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5492921A (en) * | 1977-12-20 | 1979-07-23 | Hoffmann La Roche | Peptide derivative |
| CN103204905A (en) * | 2013-03-15 | 2013-07-17 | 四川同晟生物科技有限公司 | Method for synthesizing tetra-glycylglycine |
| CN104086475A (en) * | 2014-07-15 | 2014-10-08 | 苏州天马精细化学品股份有限公司 | Preparation method of N-carbobenzoxy-L-prolinamide |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SU1410867A3 (en) | Method of hydrolysis of cellulose-containing material | |
| CN108341776B (en) | Process for synthesizing chloroquinate | |
| CN109336831B (en) | Method for recovering triazine ring from triazine ring wastewater | |
| CN105254575B (en) | A kind of synthetic method of sulphadiazine | |
| CN104817588A (en) | Preparation method of ethyl chloride | |
| RU2019103844A (en) | METHOD FOR PRODUCING ETHYLENOXIDE | |
| CN101318913B (en) | Method for preparing parachlorobenzyl isocyanic ester | |
| CN110143896A (en) | A kind of preparation method of N- benzyloxycarbonyl group-L- glycoleucine | |
| CN102659631A (en) | One-step synthesis of ethyl isocyanate | |
| CN110156640A (en) | A kind of preparation process of N- benzyloxycarbonyl-amino acid | |
| CN106986762A (en) | A kind of technique for preparing DL mandelic acids | |
| JP5734429B2 (en) | Method for producing dicyclohexyl disulfide | |
| CN108913726A (en) | A kind of technique that biochemical method prepares acrylamide | |
| CN104860843B (en) | Synthesis method of ketazine | |
| CN110078660B (en) | Preparation method of 2-chloro-5-methylpyridine | |
| CN104844459B (en) | A kind of preparation method of chloromethyl butylperoxyisopropyl carbonate | |
| CN107043343B (en) | Preparation method of L-pyroglutamic acid | |
| CN102381998A (en) | Synthetic method of gamma-aminobutyric acid | |
| CN101284809A (en) | Production method for acetic hyctro peroxide of high concentration by tower type and continuous process | |
| CN112225720A (en) | Production method of thiophene-2-acetyl chloride | |
| CN112624921A (en) | Synthesis method and application of 1-hydroxymethyl cyclopropyl acetic acid | |
| CN107011254B (en) | Synthesis and purification method of 2-amino-4-methylpyridine | |
| KR100823440B1 (en) | Method for preparing ethyl acetate of high purity from exhaust ethyl acetate | |
| US10221187B2 (en) | Method for preparing anhydrosugar alcohol using two-step hydrothermal reaction | |
| CN115181033B (en) | Catalytic synthesis method of propanil |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20190820 |
|
| RJ01 | Rejection of invention patent application after publication |