- Synthesis of 5-aminolevulinic acid with nontoxic regents and renewable methyl levulinate
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Synthesis of 5-aminolevulinic acid (5-ALA) was presented with novel bromination of biobased methyl levulinate (ML), followed by ammoniation and hydrolysis. Copper bromide (CuBr2) was employed as the bromination reagent with higher selectivity and activity instead of the conventional liquid bromine (Br2). 5-ALA was obtained in a high yield (64%) and purity (>95%) by optimum design, which is of great potential in industrialization.
- Zai, Yuxia,Feng, Yunchao,Zeng, Xianhai,Tang, Xing,Sun, Yong,Lin, Lu
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- Preparation method 5 - ALA intermediate 5 - bromoolevulinic acid ester
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The invention relates to a preparation method of 5 - ALA intermediate 5 - bromoacetyl ester, which is characterized by comprising the following steps: (S1) reaction of the urotropine and a bromine source to prepare the urotropine bromine complex. (S2) Lourotropine bromide complex and levulinic acid ester reaction. Gave 5 - bromoolevulinic acid ester. Compared with the prior art, a bromo reagent such as liquid bromine and 5 - is used directly, NBS-site bromination product yield is increased 5 - 10% or more. The defect that 3 -position bromination or multi-site bromination product is large and separation is difficult in the bromination reaction is overcome. The method is cheap and easily available in raw materials, simple and convenient to operate and suitable for large-scale preparation 5 - ALA intermediate 5 - bromolevulinic acid ester .
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Paragraph 0032; 0053; 0055-0056
(2021/09/22)
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- Method for manufacturing methyl 5-bromolevulinate and manufacturing method 5-aminolevulinic acid heyl ester hydrochloride using the same
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The present invention relates to a method of preparing methyl 5-bromolevulinate, capable of improving the yield of a final product while having stability of a product, and a method of preparing 5-aminoalkylenic acid hexyl ester hydrochloride using the same. To this end, the method of preparing methyl 5-bromolevulinate comprises: a first reaction step of mixing levulinic acid, methanol and bromine in a container and making the mixture react; a second reaction step of mixing a first product of the first reaction step, a first reactant not reacting in the first reaction step, ultrapure water and chloroform solution, and making the mixture react; an extraction step of extracting a chloroform solution layer from a first mixture formed after the second reaction step; a third reaction step of mixing the chloroform solution layer extracted in the extraction step, ethyl ether, and sodium bicarbonate saturated aqueous solution and stirring the mixture; a purification step of separating an aqueous solution layer from a second mixture formed after the third reaction step; a fourth reaction step of mixing a remaining mixture after the aqueous solution layer is separated from the second mixture with N-Hexane, and making the mixture react; a precipitation step of precipitating methyl 5-bromolevulinate in a solid state from a third mixture while quenching the third mixture formed after the fourth reaction step; and a filtering step of filtering the methyl 5-bromolevulinate in the solid state from a fourth mixture formed after the precipitation step by using a filtration device.COPYRIGHT KIPO 2019
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Paragraph 0048-0050
(2019/02/28)
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- Synthesis of thiazole derivatives bearing an incorporated Z-5-aminopent-3-enoic acid fragment
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Novel compounds bearing a joint thiazole and a Z-5-aminopent-3-enoic acid fragments have been synthesized from readily accessible 5-bromolevulinic esters through a sequence of nucleophilic substitution, bromination, Hantzsch-type heterocyclization and Gabriel-like deprotection reactions. A majority of these reactions proceed in ionic liquid media that enhances their efficiency and selectivity in comparison to the corresponding reactions in conventional organic solvents. The compounds have a significant pharmaceutical potential.
- Zavozin, Alexander G.,Ignat'Ev, Nikolai V.,Schulte, Michael,Zlotin, Sergei G.
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p. 6975 - 6980
(2013/07/26)
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- PROCESS FOR THE PREPARATION OF ALKYL 5- (DICARBOXIMIDO) LEVULINATE AND ALKYL 4-OXO-PENTENOATE
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A method of manufacturing esters of dicarboxyimidolevulinic acid and alkyl trans-4-oxo-2-pentenoate. This method includes two reaction steps, wherein the first step of said two reaction steps is a bromination of alkyl-levulinate, to obtain alkyl-(3 and 5)-bromolevulinate, and the second step of said two reaction steps is a synthesis of esters of dicarboxyimidolevulinic acid and alkyl trans-4-oxo-2-pentenoate, by reacting the alkyl-(3 and 5)-bromolevulinate obtained in said first step with dicarboxyimide anion.
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Page/Page column 6-7
(2008/06/13)
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- The synthesis and applications of 5-aminolevulinic acid (ALA) derivatives in photodynamic therapy and photodiagnosis
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A route has been developed to high-purity precursors, viz., ALA esters, to be used in photodiagnosis and photodynamic therapy. Hexyl, butyl and methyl 5-aminolevulinates are similar to the ALA acid in chemical stability and efficacy in producing the appropriate photosensitizer PpIX. Tests carried out on animal models showed the method based on the esters to be the more selective.
- Dabrowski, Zbigniew,Kwasny, Miroslaw,Kaminski, Jaroslaw,Beldowicz, Maria,Lewicka, Lidia,Obukowicz, Bozena,Kaliszewski, Miron,Pirozynska, Ewa
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p. 219 - 224
(2007/10/03)
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- THE SYNTHESIS OF A FLUORINATED ANALOGUE OF 5-AMINOLAEVULINIC ACID, A POTENTIAL INHIBITOR OF PORPHYRIN BIOSYNTHESIS
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5-Amino-2-fluorolaevulinic acid 3 has been synthesized in high yield by modification of a new route to 5-aminolaevulinic acid (ALA), involving γ-lactone intermediates.Initial studies suggest that 3 is an inhibitor of ALA dehydratase, an early enzyme of tetrapyrrole biosynthesis.
- Leeper, Finian J.,Rock, Martin
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p. 381 - 396
(2007/10/02)
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- Synthesis of 5-Aminolevulinic Acid
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A 3-step synthesis of 5-aminolevulinic acid is described. - Key words: 5-Aminolevulinic Acid
- Benedikt, Eva,Koest, Hans-Peter
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p. 1593 - 1594
(2007/10/02)
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