CN102351733B - Method for preparing 2-amino-dimethyl acetamide hydrochloride - Google Patents
Method for preparing 2-amino-dimethyl acetamide hydrochloride Download PDFInfo
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Abstract
A method for preparing 2-amino-dimethyl acetamide hydrochloride. An initial raw material is selected from commercialized raw material or easily prepared glycine methyl ester hydrochloride and is prepared into 2-amino-dimethyl acetamide hydrochloride by amino protection, aminolysis and deprotection. The invention has advantages of cheap and easily available raw material, mild reaction conditions, stable technology, a stable overall yield at 78-84%, a stable object product purity higher than 99%, and intermediates obtained by direct separation with a purity higher than 98%. Meanwhile operations of the whole production process are simple and without generation of three wastes (waste gas, waste water and industrial residue) so as to save production costs substantially. The method is suitable for large scale production and provides a new thinking and approach for preparation of 2-amino-dimethyl acetamide hydrochloride.
Description
(1) technical field:
The present invention relates to organic synthesis and prepare chemical field, particularly a kind of method of preparing 2-amino-dimethyl acetamide hydrochloride.
(2) background technology:
G-NH2 and derivative thereof are widely used in biology, medicine, chemical field always, and that synthetic G-NH2 compound is German (Koenigs E, Mylo B, Ber.1909,41:4427) such as Ernest Koenigs the earliest.Afterwards, people for find some have similar Cocaine there is toponarcosis effect but the anaesthetic that can not be addicting has synthesized hundreds of these compounds, lidocaine wherein, prilocaine, a beautiful cacaine etc. shows good anesthetic action (Dong Tingwei, paddy jade-like stone jade-like stone, Wu's generation is dizzy etc. modern Experiment of Organic Chemistry. and the .1987.312 of Shanghai translation issuing society), thereby promoted the broad research of this compounds, as be used as replacement N-(indole-2-carbonyl) G-NH2 (CN1142492) of antidiabetic, there are the inhibiting two cyclosubstituted G-NH2s (CN101213195A) of antithrombotic formation and the XA factor, the G-NH2 (CN1131144A) replacing as the anti-depressant aryl of cck receptor, the Alpha-hydroxy G-NH2 (CV1777414A) that inhibition HIV copies etc.Meanwhile, glycinamide derivative is also applied to chemical field, as N-alkyl-halo amino acetamide can be used as the ashless, without phosphorus of lubricating oil and the wear-resistant and friction adjusting additive (CN200580030478.8) without sulphur.
2-amino-dimethyl acetamide hydrochloride is as the simplest derivative of G-NH2, particularly extensive in the application of medicine, chemical field, as take its as the synthetic G-NH2 Hete rocyclic derivatives of raw material be Lp-PLA
2enzyme inhibitors, can be used for treating atherosclerosis (WO2003/042179), take that it can be used as disinfectant use in agriculture or mycocide (CN1105356A) etc. as the synthetic N-Alkylaminoacetamide compounds of raw material.2-amino-N that present stage is reported, the synthetic method of N-N,N-DIMETHYLACETAMIDE hydrochloride is mainly to take Boc-glycine as starting raw material, through ammonia solution and deprotection salify, obtain 2-amino-N, N-N,N-DIMETHYLACETAMIDE hydrochloride (Tetrahedron Letters, 1997, vol.38, #17 P.3039-3042), ammonia solution step wherein must be used condensing agent HOBt and EDC/HCl (US2008/318923) or CDI (Journal of the Chemical Society, Perkin Transactions 2:Physical Organic Chemistry (1972～1999); Nb.3; (1991); P.387～392) activating carboxy acid, must remove condensing agent again after completion of the reaction, and operation sequence is complicated, and the condensing agent raw materials cost using is higher, is not suitable for scale operation.Therefore, be to solve this difficult problem existing in prior art, suddenly wait to find one with low cost, technique is simple, is applicable to large-scale production and can creates the synthetic route of considerable economic benefit.
(3) summary of the invention:
The object of the present invention is to provide a kind of 2-of preparation amino-N; the method of N-N,N-DIMETHYLACETAMIDE hydrochloride; the all raw materials of the method are all cheap and easy to get; reaction conditions is gentle; simple to operate, process stabilizing, purity and yield is all higher; for preparation 2-amino-dimethyl acetamide hydrochloride provides a kind of new approaches that are applicable to large-scale production.
Technical scheme of the present invention: a kind of method of preparing 2-amino-dimethyl acetamide hydrochloride, is characterized in that concrete preparation process is as follows:
(1) amido protecting: glycine methyl ester hydrochloride and tert-Butyl dicarbonate are protected amino under the catalysis of alkali in ethers or varsol, the mol ratio of glycine methyl ester hydrochloride and tert-Butyl dicarbonate is 1.0: 1.0～2.0, the mol ratio of glycine methyl ester hydrochloride and alkali is 1.0: 1.0～4.0, the amount ratio of glycine methyl ester hydrochloride and ethers or varsol is 1g/5～15mL, and temperature of reaction is 0～30 ℃; After completion of the reaction, concentrate to obtain Boc-glycine methyl ester;
(2) ammonia solution: Boc-glycine methyl ester and dimethylamine are condensed into acid amides under certain pressure in ether solvent, wherein the mol ratio of Boc-glycine methyl ester and dimethylamine is 1.0: 10.0～25.0, the amount ratio of Boc-glycine methyl ester and ether solvent is 1g/5～15mL, temperature of reaction is 30～60 ℃, and reaction pressure is 0.1～1.0Mpa; After completion of the reaction, cooling, press filtration, filtrate concentrates to obtain N, N-dimethyl-Boc G-NH2;
(3) deprotection salify: N, N-dimethyl-Boc G-NH2 takes off Boc salify under acidic conditions in ethers or esters solvent, N, N-dimethyl-Boc G-NH2 and sour mol ratio are 1.0: 3.0～5.0, N, the amount ratio of N-dimethyl-Boc G-NH2 and ethers or esters solvent is 1g/5～15mL, and temperature of reaction is 30～60 ℃; After completion of the reaction, cooling, crystallization, suction filtration obtains 2-amino-dimethyl acetamide hydrochloride.
In above-mentioned said step (1), the mol ratio of glycine methyl ester hydrochloride and tert-Butyl dicarbonate is 1.0: 1.0～1.5, the mol ratio of glycine methyl ester hydrochloride and alkali is 1.0: 1.0～3.0, the amount ratio of glycine methyl ester hydrochloride and ethers or varsol is 1g/8～10mL, and temperature of reaction is 15～20 ℃.
In above-mentioned said step (2), the mol ratio of Boc-glycine methyl ester and dimethylamine is 1.0: 15.0～20.0, and the amount ratio of Boc-glycine methyl ester and ether solvent is 1g/8～10mL, and temperature of reaction is 40～45 ℃, and reaction pressure is 0.5～0.8MPa.
N in above-mentioned said step (3), N-dimethyl-Boc G-NH2 and sour mol ratio are 1.0: 3.5～4.5, N, the amount ratio of N-dimethyl-Boc G-NH2 and ethers or esters solvent is 1g/8～10mL, temperature of reaction is 40～45 ℃.
In above-mentioned said step (1), alkali is 5～20% sodium carbonate or sodium bicarbonate aqueous solution, triethylamine or N-methylmorpholine; Ethers or varsol are tetrahydrofuran (THF), methyl tertiary butyl ether, Isosorbide-5-Nitrae-dioxane or methylene dichloride.
In above-mentioned said step (2), ether solvent is tetrahydrofuran (THF), 2-methyltetrahydrofuran, methyl tertiary butyl ether or Isosorbide-5-Nitrae-dioxane.
Acid is hydrogen chloride gas or its alcohol, the aqueous solution in above-mentioned said step (3), formic acid, trifluoroacetic acid or methylsulphonic acid; Ethers or esters solvent are tetrahydrofuran (THF), Isosorbide-5-Nitrae-dioxane, ethyl acetate or isopropyl acetate.
In above-mentioned said step (1), alkali is 15% aqueous sodium carbonate, and ethers or varsol are methylene dichloride.
In above-mentioned said step (2), ether solvent is tetrahydrofuran (THF).
In above-mentioned said step (3), acid is ethanol solution of hydrogen chloride, and ethers or esters solvent are ethyl acetate.
Superiority of the present invention: raw material is cheap and easy to get; reaction conditions is gentle; process stabilizing; total recovery is stabilized in 78%～84%, and target product purity is stabilized in more than 99%, and directly separation obtains purity and more than 98% respectively walks intermediate; simultaneously because whole production process is simple to operate; can produce the three wastes hardly, greatly save production cost, be applicable to large-scale production.
(4) accompanying drawing explanation:
Fig. 1 is the related a kind of chemical equation of preparing the method for 2-amino-dimethyl acetamide hydrochloride of the present invention.
(5) embodiment:
For the interval range occurring in embodiment, be because temperature in single test is with certain the floating of there will be of reaction process, its statement is the routine statement in the synthetic field of chemical industry.
Embodiment 1:
A method of preparing 2-amino-dimethyl acetamide hydrochloride, is characterized in that concrete preparation process is as follows:
(1) amido protecting: successively to the aqueous sodium carbonate 55L (1.0eq) that adds 15% in 200L reactor; methylene dichloride 50L (5mL/g); tert-Butyl dicarbonate 17.4kg (1.0eq), main raw material glycine methyl ester hydrochloride 10kg, in 0 ± 2 ℃ of stirring reaction 2 hours.After completion of the reaction, separatory, water dichloromethane extraction, organic phase merges salt and washes rear Boc-glycine methyl ester 14.5kg, yield 96.2%, the GC purity 98.8% of concentrating to obtain.
The nuclear magnetic data of Boc-glycine methyl ester is as follows:
1h NMR (300MHZ, CDCl3), δ 1.38 (H of 3 methyl of the tertiary butyl), δ 3.68 (H on methyl esters), δ 3.90 (H on methylene radical), δ 7.90 (H on amino)
(2) ammonia solution: add main raw material Boc-glycine methyl ester 8kg successively in 200L autoclave, methyl tertiary butyl ether 40L (5mL/g), with nitrogen, 200L autoclave is replaced after 3 times, be pressed into 19.1kg (10.0eq) dimethylamine, be warming up to 30 ± 2 ℃, control pressure is at 0.1 ± 0.05MPa, stirring reaction 24h.After completion of the reaction, by reaction system suction filtration, filtrate concentrates to obtain N, N-dimethyl-Boc G-NH2 7.8kg, yield 91.2%, GC purity 98.6%.
N, the nuclear magnetic data of N-dimethyl-Boc G-NH2 is as follows:
1h NMR (300MHZ, CDCl3), δ 1.39 (H of 3 methyl of the tertiary butyl), δ 2.86 (H of two methyl of the upper replacement of N), δ 3.80 (H on methylene radical), δ 7.90 (H on amino)
(3) deprotection salify: add isopropyl acetate 80L (5mL/g) successively in 200L reactor; main raw material N, N-dimethyl-Boc G-NH2 16kg, in 30 ± 2 ℃; drip 25% hydrogen chloride methanol solution 35kg (3.0eq), drip complete stirring reaction 1 hour.After completion of the reaction, cooling crystallization obtains 2-amino-dimethyl acetamide hydrochloride 10kg, yield 91.2%, GC purity 99.2%.
The nuclear magnetic data of 2-amino-dimethyl acetamide hydrochloride is as follows:
1h NMR (300MHZ, CDCl3), δ 2.84 (H of two methyl of the upper replacement of N), δ 3.50 (H on methylene radical), δ 5.07 (H on amino).
Embodiment 2:
A method of preparing 2-amino-dimethyl acetamide hydrochloride, is characterized in that concrete preparation process is as follows:
(1) amido protecting: add main raw material glycine methyl ester hydrochloride 1kg successively in 50L reaction flask; methyl tertiary butyl ether 15L (15mL/g); N-methylmorpholine 3.3kg (4.0eq); be cooled to 30 ± 2 ℃; drip tert-Butyl dicarbonate 3.5kg (2.0eq), drip and finish in 30 ± 2 ℃ of insulation reaction 1～2h.After completion of the reaction, be concentrated into solvent-freely, add water 6L, insulated and stirred 1～2h, filters to obtain Boc-glycine methyl ester, dries to obtain 1.44kg, yield 95.5%, GC purity 98.9%;
The nuclear magnetic data of Boc-glycine methyl ester is as follows:
1h NMR (300MHZ, CDCl3), δ 1.42 (H of 3 methyl of the tertiary butyl), δ 3.56 (H on methyl esters), δ 3.88 (H on methylene radical), δ 7.87 (H on amino).
(2) ammonia solution: add main raw material Boc-glycine methyl ester 100g successively in 5L autoclave, 1,4-dioxane 1.5L (15mL/g), with nitrogen, 5L autoclave is replaced after 3 times, be pressed into 596g (25.0eq) dimethylamine, be warming up to 60 ± 2 ℃, control pressure is at 1.0 ± 0.05MPa, stirring reaction 18h.After completion of the reaction, by reaction system suction filtration, after filtrate is concentrated, cooling crystallization obtains N, N-dimethyl-Boc G-NH2 99g, yield 92.6%, GC purity 99.5%;
N, the nuclear magnetic data of N-dimethyl-Boc G-NH2 is as follows:
1h NMR (300MHZ, CDCl3), δ 1.42 (H of 3 methyl of the tertiary butyl), δ 2.92 (H of two methyl of the upper replacement of N), δ 3.90 (H on methylene radical), δ 7.99 (H on amino).
(3) deprotection salify: in 100L reactor, add Isosorbide-5-Nitrae dioxane 45L (15mL/g) successively, main raw material N, N-dimethyl-Boc G-NH2 3kg, passes into hydrogen chloride gas 2.7kg (5.0eq) in 60 ± 2 ℃, is incubated 0.5 hour.After completion of the reaction, cooling crystallization obtains 2-amino-dimethyl acetamide hydrochloride 1.9kg, yield 92.4%, GC purity 99.6%.
The nuclear magnetic data of 2-amino-dimethyl acetamide hydrochloride is as follows:
1h NMR (300MHZ, CDCl3), δ 2.95 (H of two methyl of the upper replacement of N), δ 3.60 (H on methylene radical), δ 5.15 (H on amino).
Embodiment 3:
A method of preparing 2-amino-dimethyl acetamide hydrochloride, is characterized in that concrete preparation process is as follows:
(1) amido protecting: add main raw material glycine methyl ester hydrochloride 25kg successively in 500L reactor; tetrahydrofuran (THF) 200L (8mL/g); triethylamine 50.4kg (2.5eq); be cooled to 15 ± 2 ℃; drip tert-Butyl dicarbonate 52.2kg (1.2eq), drip and finish in 15 ± 2 ℃ of insulation reaction 1～2h.After completion of the reaction, add water, separatory, organic phase is concentrated, cooling, crystallization obtains Boc-glycine methyl ester 36kg, yield 95.5%, GC purity 99.4%.
The nuclear magnetic data of Boc-glycine methyl ester is as follows:
1h NMR (300MHZ, CDCl3), δ 1.40 (H of 3 methyl of the tertiary butyl), δ 3.67 (H on methyl esters), δ 3.92 (H on methylene radical), δ 7.95 (H on amino).
(2) ammonia solution: add main raw material Boc-glycine methyl ester 20kg successively in 500L autoclave, tetrahydrofuran (THF) 200L (10mL/g), with nitrogen, 500L autoclave is replaced after 3 times, be pressed into 86kg (18.0eq) dimethylamine, be warming up to 40 ± 2 ℃, control pressure is at 0.4 ± 0.05MPa, stirring reaction 18h.After completion of the reaction, by reaction system suction filtration, after filtrate is concentrated, cooling crystallization obtains N, N-dimethyl-Boc G-NH2 20.2kg, yield 94.5%, GC purity 98.8%.
N, the nuclear magnetic data of N-dimethyl-Boc G-NH2 is as follows:
1h NMR (300MHZ, CDCl3), δ 1.40 (H of 3 methyl of the tertiary butyl), δ 2.90 (H of two methyl of the upper replacement of N), δ 3.85 (H on methylene radical), δ 7.95 (H on amino).
(3) deprotection salify: add ethyl acetate 200L (8mL/g) successively in 500L reactor; main raw material N; N-dimethyl-Boc G-NH2 25kg, drips 34% ethanol solution of hydrogen chloride 53kg (4.0eq), a complete stirring reaction 1 hour in 40 ± 2 ℃.After completion of the reaction, cooling, crystallization obtains 2-amino-dimethyl acetamide hydrochloride 15.5kg, yield 90.5%, GC purity 99.0%.
The nuclear magnetic data of 2-amino-dimethyl acetamide hydrochloride is as follows:
1h NMR (300MHZ, CDCl3), δ 2.90 (H of two methyl of the upper replacement of N), δ 3.54 (H on methylene radical), δ 5.12 (H on amino).
As can be seen here, in the present invention, the method for the disclosed 2-of preparation amino-dimethyl acetamide hydrochloride can obtain the target product that purity is high, and purity is stabilized in more than 99.0%, this synthetic method is raw materials used to be easy to get, reaction conditions is gentle, and technique is simple, and total recovery is stabilized in 78%～82%, whole production process is simple to operate, can produce the three wastes hardly, for preparation 2-amino-dimethyl acetamide hydrochloride provides a kind of new thinking and method.
Claims (10)
1. a method of preparing 2-amino-dimethyl acetamide hydrochloride, is characterized in that concrete preparation process is as follows:
(1) amido protecting: glycine methyl ester hydrochloride and tert-Butyl dicarbonate are protected amino under the catalysis of alkali in ethers or varsol, the mol ratio of glycine methyl ester hydrochloride and tert-Butyl dicarbonate is 1.0: 1.0～2.0, the mol ratio of glycine methyl ester hydrochloride and alkali is 1.0: 1.0～4.0, the amount ratio of glycine methyl ester hydrochloride and ethers or varsol is 1g/5～15mL, and temperature of reaction is 0～30 ℃; After completion of the reaction, concentrate to obtain Boc-glycine methyl ester;
(2) ammonia solution: Boc-glycine methyl ester and dimethylamine are condensed into acid amides under certain pressure in ether solvent, wherein the mol ratio of Boc-glycine methyl ester and dimethylamine is 1.0: 10.0～25.0, the amount ratio of Boc-glycine methyl ester and ether solvent is 1g/5～15mL, temperature of reaction is 30～60 ℃, and reaction pressure is 0.1～1.0Mpa; After completion of the reaction, cooling, press filtration, filtrate concentrates to obtain N, N-dimethyl-Boc G-NH2;
(3) deprotection salify: N, N-dimethyl-Boc G-NH2 takes off Boc salify under acidic conditions in ethers or esters solvent, N, N-dimethyl-Boc G-NH2 and sour mol ratio are 1.0: 3.0～5.0, N, the amount ratio of N-dimethyl-Boc G-NH2 and ethers or esters solvent is 1g/5～15mL, and temperature of reaction is 30～60 ℃; After completion of the reaction, cooling, crystallization, suction filtration obtains 2-amino-dimethyl acetamide hydrochloride.
2. according to the said a kind of 2-amino-N for preparing of claim 1, the method of N-N,N-DIMETHYLACETAMIDE hydrochloride, the mol ratio that it is characterized in that the middle glycine methyl ester hydrochloride of said step (1) and tert-Butyl dicarbonate is 1.0: 1.0～1.5, the mol ratio of glycine methyl ester hydrochloride and alkali is 1.0: 1.0～3.0, the amount ratio of glycine methyl ester hydrochloride and ethers or varsol is 1g/8～10mL, and temperature of reaction is 15～20 ℃.
3. according to the said a kind of 2-amino-N for preparing of claim 1, the method of N-N,N-DIMETHYLACETAMIDE hydrochloride, the mol ratio that it is characterized in that the middle Boc-glycine methyl ester of said step (2) and dimethylamine is 1.0: 15.0～20.0, the amount ratio of Boc-glycine methyl ester and ether solvent is 1g/8～10mL, temperature of reaction is 40～45 ℃, and reaction pressure is 0.5～0.8MPa.
4. according to the said a kind of 2-amino-N for preparing of claim 1, the method of N-N,N-DIMETHYLACETAMIDE hydrochloride, it is characterized in that N in said step (3), N-dimethyl-Boc G-NH2 and sour mol ratio are 1.0: 3.5～4.5, N, the amount ratio of N-dimethyl-Boc G-NH2 and ethers or esters solvent is 1g/8～10mL, and temperature of reaction is 40～45 ℃.
5. according to a kind of said method of preparing 2-amino-dimethyl acetamide hydrochloride of claim 1, it is characterized in that in said step (1), alkali is 5～20% sodium carbonate or sodium bicarbonate aqueous solution, triethylamine or N-methylmorpholine; Ethers or varsol are tetrahydrofuran (THF), methyl tertiary butyl ether, Isosorbide-5-Nitrae-dioxane or methylene dichloride.
6. according to a kind of said method of preparing 2-amino-dimethyl acetamide hydrochloride of claim 1, it is characterized in that in said step (2), ether solvent is tetrahydrofuran (THF), 2-methyltetrahydrofuran, methyl tertiary butyl ether or Isosorbide-5-Nitrae-dioxane.
7. according to a kind of said method of preparing 2-amino-dimethyl acetamide hydrochloride of claim 1, it is characterized in that in said step (3) that acid is for hydrogen chloride gas or its alcohol, the aqueous solution, formic acid, trifluoroacetic acid or methylsulphonic acid; Ethers or esters solvent are tetrahydrofuran (THF), Isosorbide-5-Nitrae-dioxane, ethyl acetate or isopropyl acetate.
8. according to a kind of said method of preparing 2-amino-dimethyl acetamide hydrochloride of claim 5, it is characterized in that the middle alkali of said step (1) is 15% aqueous sodium carbonate, ethers or varsol are methylene dichloride.
9. according to a kind of said method of preparing 2-amino-dimethyl acetamide hydrochloride of claim 6, it is characterized in that in said step (2), ether solvent is tetrahydrofuran (THF).
10. according to a kind of said method of preparing 2-amino-dimethyl acetamide hydrochloride of claim 7, it is characterized in that in said step (3), acid is ethanol solution of hydrogen chloride, ethers or esters solvent are ethyl acetate.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US4639468A (en) * | 1979-03-22 | 1987-01-27 | Continental Pharma Inc. | Derivatives of glycinamide, their preparation and their use |
| CN1180352A (en) * | 1995-04-14 | 1998-04-29 | 贝林格尔·英格海姆公司 | Aryl glycinamide derivatives, methods of producing these substances and pharmaceutical compositions containing such compounds |
| US20080318923A1 (en) * | 2005-01-28 | 2008-12-25 | Taisho Pharmaceutical Co., Ltd. | 1,3-Dihydro-2H-Indole-2-One Compound and Pyrrolidine-2-One Compound Fused With Aromatic Heterocycle |
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| MX155250A (en) * | 1982-06-21 | 1988-02-10 | Acf Ind Inc | IMPROVEMENTS TO A CARBURATION SYSTEM FUEL PUMP FOR AUTOMOBILES |
| JPH0597789A (en) * | 1991-10-03 | 1993-04-20 | Nippon Chibagaigii Kk | Alpha-hydroxyglycinamide derivative and its production |
| JP3425453B2 (en) * | 1993-05-26 | 2003-07-14 | 日本製紙株式会社 | Pulp bleaching microorganism and pulp bleaching method using the same |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US4639468A (en) * | 1979-03-22 | 1987-01-27 | Continental Pharma Inc. | Derivatives of glycinamide, their preparation and their use |
| CN1180352A (en) * | 1995-04-14 | 1998-04-29 | 贝林格尔·英格海姆公司 | Aryl glycinamide derivatives, methods of producing these substances and pharmaceutical compositions containing such compounds |
| US20080318923A1 (en) * | 2005-01-28 | 2008-12-25 | Taisho Pharmaceutical Co., Ltd. | 1,3-Dihydro-2H-Indole-2-One Compound and Pyrrolidine-2-One Compound Fused With Aromatic Heterocycle |
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