CN106947795B - Method for synthesizing 2-thiophene ethylamine through biocatalysis - Google Patents
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- HVLUYXIJZLDNIS-UHFFFAOYSA-N 2-thiophen-2-ylethanamine Chemical compound NCCC1=CC=CS1 HVLUYXIJZLDNIS-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 238000000034 method Methods 0.000 title claims abstract description 23
- 230000002194 synthesizing effect Effects 0.000 title abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 31
- 241000194108 Bacillus licheniformis Species 0.000 claims abstract description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000001963 growth medium Substances 0.000 claims abstract description 15
- UTPOWFFIBWOQRK-ONEGZZNKSA-N 2-[(e)-2-nitroethenyl]thiophene Chemical compound [O-][N+](=O)\C=C\C1=CC=CS1 UTPOWFFIBWOQRK-ONEGZZNKSA-N 0.000 claims abstract description 12
- 230000002210 biocatalytic effect Effects 0.000 claims abstract description 10
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 7
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims abstract description 5
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 5
- 238000001816 cooling Methods 0.000 claims abstract description 5
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 claims abstract description 5
- 239000008103 glucose Substances 0.000 claims abstract description 5
- 229910000402 monopotassium phosphate Inorganic materials 0.000 claims abstract description 5
- 235000019796 monopotassium phosphate Nutrition 0.000 claims abstract description 5
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000000047 product Substances 0.000 claims abstract description 5
- 230000001954 sterilising effect Effects 0.000 claims abstract description 5
- 239000006228 supernatant Substances 0.000 claims abstract description 5
- 230000004913 activation Effects 0.000 claims abstract description 4
- 238000001035 drying Methods 0.000 claims abstract description 4
- 238000005406 washing Methods 0.000 claims abstract description 4
- 230000003213 activating effect Effects 0.000 claims abstract description 3
- 239000007864 aqueous solution Substances 0.000 claims abstract description 3
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims abstract description 3
- 239000000243 solution Substances 0.000 claims description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000012295 chemical reaction liquid Substances 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 238000003912 environmental pollution Methods 0.000 abstract description 4
- 238000000926 separation method Methods 0.000 abstract description 3
- 238000006555 catalytic reaction Methods 0.000 abstract description 2
- 238000004821 distillation Methods 0.000 abstract description 2
- 230000008569 process Effects 0.000 abstract description 2
- 230000000052 comparative effect Effects 0.000 description 8
- 239000003638 chemical reducing agent Substances 0.000 description 5
- 238000006722 reduction reaction Methods 0.000 description 5
- 239000003814 drug Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 230000002526 effect on cardiovascular system Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GCSBLDVEMVRXHG-UHFFFAOYSA-N 1-nitroethene;thiophene Chemical compound C=1C=CSC=1.[O-][N+](=O)C=C GCSBLDVEMVRXHG-UHFFFAOYSA-N 0.000 description 1
- 229940124125 5 Lipoxygenase inhibitor Drugs 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 101000783577 Dendroaspis angusticeps Thrombostatin Proteins 0.000 description 1
- 101000783578 Dendroaspis jamesoni kaimosae Dendroaspin Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000000867 Lipoxygenase Inhibitor Substances 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- ZQRGREQWCRSUCI-UHFFFAOYSA-N [S].C=1C=CSC=1 Chemical compound [S].C=1C=CSC=1 ZQRGREQWCRSUCI-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940127218 antiplatelet drug Drugs 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000000055 hyoplipidemic effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- -1 lithium aluminum hydride Chemical compound 0.000 description 1
- 238000011177 media preparation Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000000106 platelet aggregation inhibitor Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229960002961 ticlopidine hydrochloride Drugs 0.000 description 1
- MTKNGOHFNXIVOS-UHFFFAOYSA-N ticlopidine hydrochloride Chemical compound [H+].[Cl-].ClC1=CC=CC=C1CN1CC(C=CS2)=C2CC1 MTKNGOHFNXIVOS-UHFFFAOYSA-N 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
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- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
- C12N1/20—Bacteria; Culture media therefor
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- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
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- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
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- Virology (AREA)
- Tropical Medicine & Parasitology (AREA)
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Abstract
A method for synthesizing 2-thiophene ethylamine by biological catalysis comprises the steps of preparing aqueous solution from glucose, disodium hydrogen phosphate and potassium dihydrogen phosphate according to a certain proportion, sterilizing and cooling to obtain a bacillus licheniformis culture medium; then according to a certain thallus concentration, activating in a shaking table at a constant temperature; and dissolving the 2-nitrovinyl thiophene, adding the dissolved 2-nitrovinyl thiophene into an activation culture medium for biocatalytic reaction, then carrying out centrifugal separation, extracting supernatant with ethyl acetate, washing, drying, and carrying out reduced pressure distillation to obtain a product 2-thiophene ethylamine. The method has the remarkable characteristics and progresses of simple process, high synthesis yield, low cost and less environmental pollution.
Description
Technical Field
The invention relates to a method for synthesizing 2-thiophene ethylamine, in particular to a method for synthesizing 2-thiophene ethylamine by biologically catalyzing and reducing 2-nitrovinyl thiophene with bacillus licheniformis, belonging to the technical field of chemical industry and medicine.
Background
The 2-thiophene ethylamine is an important intermediate for synthesizing ticlopidine hydrochloride which is a medicament for treating cardiovascular and cerebrovascular diseases, and is also an intermediate of other biological active medicaments such as a hypolipidemic medicament, a platelet aggregation inhibitor, a cardiovascular vasodilator, a 5-lipoxygenase inhibitor, a plurality of antibacterial agents and the like. The most common synthetic method reported in the literature at present is to prepare 2-thiophenecarboxaldehyde by taking thiophene as a raw material, then react with nitromethane to obtain 2-nitrovinyl thiophene, and finally reduce to obtain 2-thiopheneethylamine. In the designed synthetic route, the double bond and the nitro group are reduced in the last step of reduction reaction, and the molecules contain sulfur, so that the synthetic step has high cost and harsh reaction conditions. The main reduction methods at present are the following three: (1) reducing by using sodium borohydride as a reducing agent: the yield of the method is 75%, but the consumption of reducing agents and solvents is large, and the cost is high; (2) reducing by using lithium aluminum hydride as a reducing agent: the reducing agent is easy to cause explosion, is expensive and is generally only used in laboratories; (3) reducing by using hydrogen as a reducing agent: the method needs to carry out nitro reduction and double bond reduction step by step, the activity of the catalyst is inhibited by the thiophene sulfur, the yield is low, the process needs to be carried out at high temperature and high pressure, and the safety risk is high.
The methods do not accord with three major trends of high-efficiency reducibility, atom economy and environmental protection of organic synthesis. The invention adopts a biological catalytic reduction method, and the method has the characteristics of high efficiency, strong selectivity, low cost, simple device, less environmental pollution and the like, and has remarkable advantages.
Disclosure of Invention
The invention aims to provide a synthesis method with mild reaction conditions, simple operation, high yield and low cost aiming at the defect of high cost of the existing chemical synthesis technology, in particular to a synthesis method for reducing 2-nitrovinyl thiophene into 2-thiophene ethylamine by using microorganisms with almost no environmental pollution.
The above object of the present invention is achieved by the following means.
A method for biocatalytic synthesis of 2-thienylethylamine, the method comprising the steps of:
1) preparation of culture medium for bacillus licheniformis
Adding water, glucose, disodium hydrogen phosphate and potassium dihydrogen phosphate into a vessel according to the mass ratio of 1000: 30: 7: 6 to prepare an aqueous solution, adjusting the pH to be =8, sterilizing for 30 min, and cooling to obtain a bacillus licheniformis culture medium;
2) activation of Bacillus licheniformis
Adding the bacillus licheniformis according to the mass ratio of the solution of the bacillus licheniformis culture medium to the bacillus licheniformis of 10: 1, and activating for 1 hour at the constant temperature of 37 ℃ and the rotation speed of 180 r/min in a shaking table;
3) synthesis of 2-thiopheneethylamine
Dissolving 2-nitrovinyl thiophene in tetrahydrofuran, adding 5 g/L of reactant into an activated culture medium, carrying out biocatalytic reaction for 96 hours in a shaking table at 37 ℃ and the rotation speed of 180 r/min, keeping the pH =8 during the reaction, centrifugally separating reaction liquid after the reaction, extracting supernatant with ethyl acetate, washing, drying, and distilling under reduced pressure to obtain the product 2-thiophene ethylamine.
Wherein, the concentration of the bacillus licheniformis liquid is as follows: 5.0*109cfu/mL。
Compared with the existing chemical method for synthesizing 2-thiophene ethylamine, the method for synthesizing 2-thiophene ethylamine by biological catalysis has the following three substantial characteristics and remarkable progress.
Firstly, the method adopts the bacillus licheniformis to reduce double bonds and nitro groups in the 2-nitroethylene thiophene in one step, thereby greatly reducing the cost, and having mild reaction conditions and simple and convenient operation.
Secondly, the synthetic route of the method is environment-friendly and pollution-free. The reduction preparation of the 2-thiophene ethylamine by a chemical method can cause a certain degree of environmental pollution, and the bacillus licheniformis is nontoxic and harmless and has high yield.
Thirdly, the used bacillus licheniformis is activated and then reused, and the production cost is further reduced.
Detailed Description
In order to clearly illustrate the embodiments of the present invention, the following further describes the embodiments of the present invention.
Example 1
Dissolving 3 g of glucose, 0.7 g of disodium hydrogen phosphate and 0.6 g of potassium dihydrogen phosphate in 100 mL of water, adjusting the pH to be =8, sterilizing for 30 min, and cooling to obtain a bacillus licheniformis culture medium;
10 g of Bacillus licheniformis was added to the culture medium and activated for 1 hour in a shaker at a constant temperature of 37 ℃ at a rotation speed of 180 rpm.
Dissolving 0.5g of 2-nitrovinyl thiophene in 5 mL of tetrahydrofuran, adding the solution into an activated culture medium solution, carrying out biocatalytic reaction for 96 hours in a shaking table at 37 ℃ and a rotation speed of 180 revolutions per minute, keeping pH =8 during the reaction, carrying out centrifugal separation on a reaction solution after the reaction, extracting a supernatant with an ethyl acetate solvent, washing with saturated saline, drying with anhydrous sodium sulfate, and carrying out reduced pressure distillation to obtain a product 2-thiophene ethylamine with the yield of 75.5%.
Example 2
Activation and reutilization of bacillus licheniformis
Dissolving 3 g of glucose, 0.7 g of disodium hydrogen phosphate and 0.6 g of potassium dihydrogen phosphate in 100 mL of water, adjusting the pH to be =8, sterilizing for 30 min, and cooling to obtain a bacillus licheniformis culture medium;
15 g of Bacillus licheniformis obtained by centrifugal separation in example 1 was added into the culture medium, and a solution consisting of 0.5g of 2-nitrovinylthiophene and 5 mL of tetrahydrofuran was added, biocatalytic reaction was carried out in a shaker at 37 ℃ and a rotation speed of 180 rpm for 96 hours, the reaction was carried out while maintaining pH =8, after the reaction, the reaction solution was centrifugally separated, the supernatant was extracted with an ethyl acetate solvent, washed with saturated saline, dried with anhydrous sodium sulfate, and distilled under reduced pressure to obtain 2-thienylethylamine with a yield of 73.0%.
Comparative example 1
This example differs from example 1 in that yeast was added to the medium solution instead of Bacillus licheniformis, and the other experimental steps and reaction conditions were the same as in example 1, yielding a yield of 65.8% 2-thienylethylamine. The yield was lower than in example 1.
Comparative example 2
This example differs from example 1 in that the pH of the culture broth was adjusted by dropping 10% NaOH solution or 2 mol/L HCl solution during the media preparation and biocatalysis to pH =4, pH =5, pH =6, pH =7 and pH =9, respectively, and other experimental steps and reaction conditions were the same as example 1, yielding yields of 2-thiopheneethylamine of 25.8%, 34.5%, 58.9%, 72.3% and 53.2%, respectively. The yields are all lower than in example 1.
Comparative example 3
This example is different from example 1 in that the reaction temperature was changed to 30 ℃, 32 ℃, 35 ℃, 40 ℃ and 42 ℃ during the biocatalytic reaction, and other experimental steps and reaction conditions were the same as example 1, to obtain yields of 2-thienylethylamine of 53.2%, 58.3%, 65.9%, 67.8% and 40.2%, respectively. The yields are all lower than in example 1.
Comparative example 4
This example is different from example 1 in that the reaction time was changed to 24 hours, 48 hours, 72 hours, 120 hours, 144 hours and 168 hours during the biocatalytic reaction, and the other experimental procedures and reaction conditions were the same as example 1, to obtain yields of 2-thienylethylamine of 20.7%, 45.9%, 65.8%, 71.3%, 66.6% and 52.0%, respectively. The yields are all lower than in example 1.
Comparative example 5
This example differs from example 1 in that the starting 2-nitrovinylthiophene, having different masses of 0.2 g, 0.4 g, 0.6 g, 0.8 g and 1.0 g, respectively, was dissolved in 5 mL of tetrahydrofuran. The other experimental procedures and reaction conditions were the same as in example 1, and the yields of 2-thienylethylamine were 45.9%, 74.3%, 66.5%, 52.0% and 35.7%, respectively. The yields are all lower than in example 1.
Comparative example 6
This example differs from example 1 in that different masses of Bacillus licheniformis were added to the medium solution at 5g, 8 g, 12g, 15 g and 20 g, respectively, and activated in a shaker at a rotation speed of 180 rpm at a constant temperature of 37 ℃ for 1 hour to obtain an activated Bacillus licheniformis culture solution. The other experimental procedures and reaction conditions were the same as in example 1, and the yields of 2-thienylethylamine were 45.5%, 68.3%, 74.6%, 62.0% and 55.7%, respectively. The yields are all lower than in example 1.
Comparative example 7
This example differs from example 1 in that 2-nitrovinylthiophene was dissolved in different solvents, methanol, ethanol and dioxane, respectively. The other experimental procedures and reaction conditions were the same as in example 1, and the yields of 2-thienylethylamine were 56.2%, 65.4% and 68.1%, respectively. The yields are all lower than in example 1.
From example 1 to comparative example 7, it can be seen that the reaction process of the present invention is the optimum process for preparing 2-thienylethylamine by 2-nitrovinylthiophene biocatalytic reaction, and changes in reaction conditions all result in a decrease in product yield.
It should be understood that the above-mentioned embodiments of the present invention are only examples for clearly illustrating the present invention, and are not intended to limit the embodiments of the present invention, and it will be obvious to those skilled in the art that other variations or modifications may be made on the basis of the above description, and all embodiments may not be exhaustive, and all obvious variations or modifications may be included within the scope of the present invention.
Claims (1)
1. A method for biocatalytic synthesis of 2-thienylethylamine, the method comprising the steps of:
1) preparation of culture medium for bacillus licheniformis
Adding water, glucose, disodium hydrogen phosphate and potassium dihydrogen phosphate into a vessel according to the mass ratio of 1000: 30: 7: 6 to prepare an aqueous solution, adjusting the pH to be =8, sterilizing for 30 min, and cooling to obtain a bacillus licheniformis culture medium;
2) activation of Bacillus licheniformis
Adding the bacillus licheniformis according to the mass ratio of the solution of the bacillus licheniformis culture medium to the bacillus licheniformis of 10: 1, and activating for 1 hour at the constant temperature of 37 ℃ and the rotation speed of 180 r/min in a shaking table;
3) synthesis of 2-thiopheneethylamine
Dissolving 2-nitrovinyl thiophene in tetrahydrofuran, adding 5 g/L of reactant into an activated culture medium, carrying out biocatalytic reaction for 96 hours in a shaking table at 37 ℃ and the rotation speed of 180 r/min, keeping the pH =8 during the reaction, centrifugally separating reaction liquid after the reaction, extracting supernatant with ethyl acetate, washing, drying, and distilling under reduced pressure to obtain the product 2-thiophene ethylamine.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101555460A (en) * | 2009-01-09 | 2009-10-14 | 上海市农药研究所 | Bacillus licheniformis and application thereof |
| CN102659753A (en) * | 2012-05-11 | 2012-09-12 | 太原理工大学 | Synthetic method of 2-thiofuran ethylamine |
| WO2017003721A1 (en) * | 2015-06-29 | 2017-01-05 | Noramco, Inc. | Process for the preparation of lisdexamfetamine and related derivatives |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101555460A (en) * | 2009-01-09 | 2009-10-14 | 上海市农药研究所 | Bacillus licheniformis and application thereof |
| CN102659753A (en) * | 2012-05-11 | 2012-09-12 | 太原理工大学 | Synthetic method of 2-thiofuran ethylamine |
| WO2017003721A1 (en) * | 2015-06-29 | 2017-01-05 | Noramco, Inc. | Process for the preparation of lisdexamfetamine and related derivatives |
Non-Patent Citations (2)
| Title |
|---|
| Extracellular biosynthesis of silver nanoparticles by the culture supernatant of Bacillus licheniformis;K. Kalishwaralal et al;《Materials Letters》;20080630;第62卷;第4411-4413页 * |
| 地衣芽孢杆菌R08吸附和还原钯（Pd2+)的研究;林种玉等;《科学通报》;20020331(第3期);第357-360页 * |
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