109258-71-1

Usage

Uses

Used in Organic Synthesis:
Methyl 5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-oxopentanoate serves as a valuable building block in organic synthesis, utilized for the creation of a wide range of pharmaceuticals and organic molecules. Its diverse reactivity allows for the development of various chemical reactions and synthetic methodologies.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, methyl 5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-oxopentanoate is employed as a key intermediate for the synthesis of bioactive molecules and pharmaceuticals. Its unique structure and functional groups enable the design and synthesis of new compounds with potential therapeutic properties.
Used in the Development of New Chemical Reactions:
Methyl 5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-oxopentanoate is also used as a tool for developing innovative chemical reactions and synthetic strategies in organic chemistry. Its presence in various reaction schemes can lead to the discovery of more efficient and selective synthetic routes for complex organic molecules.
Used in Pharmaceutical Industry:
Methyl 5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-oxopentanoate is used as a precursor in the pharmaceutical industry for the synthesis of various drugs. Its versatile reactivity and unique structure make it a promising candidate for the development of new therapeutic agents with improved efficacy and selectivity.

Upstream product

• 62024-36-6 5-chloro-4-oxopentanoic acid methyl ester 
• 1074-82-4 potassium phtalimide 
• 136918-14-4 phthalimide 
• 53856-93-2 methyl 5-bromo-4-oxopentanoate 
• 123-76-2 levulinic acid 
• 95678-51-6 3-bromo-4-oxopentanoic acid methyl ester 
• 624-45-3 levulinic acid methyl ester 
• 1490-25-1 succinic acid monomethylester chloride 
• 58960-19-3 2-{[5-oxotetrahydrofuran-2-yl]methyl}-1H-isoindole-1,3(2H)-dione 
• 1729-32-4 5-iodomethyl-dihydro-furan-2-one 
• 135119-69-6 Methyl 4-hydroxy-5-phthalimidopentanoate 

Downstream Products

• 5451-09-2 5-aminolevulinic acid hydrochloride 
• 142896-53-5 N-(2-carboxybenzoyl)-5-amino-4-oxopentanoic acid 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 79416-27-6 methyl aminolevulinate 
• 99310-57-3 4-(2-carboxyethyl)imidazolin-2-one 

Relevant academic research and scientific papers

Synthesis of 5-aminolevulinic acid with nontoxic regents and renewable methyl levulinate

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.

Preparation method 5 - ALA intermediate 5 - bromoolevulinic acid ester

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 .

Method for manufacturing methyl 5-bromolevulinate and manufacturing method 5-aminolevulinic acid heyl ester hydrochloride using the same

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

Synthesis of thiazole derivatives bearing an incorporated Z-5-aminopent-3-enoic acid fragment

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.

PROCESS FOR THE PREPARATION OF ALKYL 5- (DICARBOXIMIDO) LEVULINATE AND ALKYL 4-OXO-PENTENOATE

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.

The synthesis and applications of 5-aminolevulinic acid (ALA) derivatives in photodynamic therapy and photodiagnosis

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.

THE SYNTHESIS OF A FLUORINATED ANALOGUE OF 5-AMINOLAEVULINIC ACID, A POTENTIAL INHIBITOR OF PORPHYRIN BIOSYNTHESIS

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.

Synthesis of 5-Aminolevulinic Acid

A 3-step synthesis of 5-aminolevulinic acid is described. - Key words: 5-Aminolevulinic Acid