48172-10-7

Basic information

• Product Name: (2S)-4-(1,3-Dioxoisoindolin-2-yl)-2-hydroxybutanoic acid
• Synonyms: 2-Hydroxy-4-phthalimidobutanoicacid;1,3-DIHYDRO-ALPHA-HYDROXY-1,3-DIOXO-2H-ISOINDOLE-2-BUTANOIC ACID;(2S)-4-(1,3-DIOXOISOINDOLIN-2-YL)-2-HYDROXYBUTANOIC ACID;2-HYDROXY-4-PHTHALIMIDOBUTYRIC ACID;4-PHTHALIMIDO-2-HYDROXY BUTYRIC ACID;(S)-(+)-ALPHA-HYDROXY-1,3-DIOXO-2-ISOINDOLINEBUTYRIC ACID;(S)-(+)-2-HYDROXY-4-PHTHALIMIDOBUTYRIC ACID;S-4-Phthalimido -2- hydroxybutyric acid
• CAS NO: 48172-10-7
• Molecular Formula: C₁₂H₁₁NO₅
• Molecular Weight: 249.22
• Product Categories: chiral;API intermediates;N-Substituted Maleimides, Succinimides & Phthalimides;N-Substituted Phthalimides;Chiral Building Blocks;Heterocyclic Building Blocks;Indoles
• Mol File: 48172-10-7.mol

Chemical Properties

• Melting Point: 157-159 °C(lit.)
• Boiling Point: 392.32°C (rough estimate)
• Flash Point: 264.1 °C
• Appearance: white to light yellow crystal powder
• Density: 1.3189 (rough estimate)
• Vapor Pressure: 2.37E-11mmHg at 25°C
• Refractive Index: 6 ° (C=1, MeOH)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: almost transparency in Methanol
• PKA: 3.67±0.10(Predicted)
• CAS DataBase Reference: (2S)-4-(1,3-Dioxoisoindolin-2-yl)-2-hydroxybutanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-4-(1,3-Dioxoisoindolin-2-yl)-2-hydroxybutanoic acid(48172-10-7)
• EPA Substance Registry System: (2S)-4-(1,3-Dioxoisoindolin-2-yl)-2-hydroxybutanoic acid(48172-10-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• Hazardous Substances Data: 48172-10-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(2S)-4-(1,3-Dioxoisoindolin-2-yl)-2-hydroxybutanoic acid is used as a key intermediate in the preparation method of plazomicin. Its application in this context is aimed at simplifying the operational process and improving the overall yield of the final product, which is an important antibiotic used to treat various bacterial infections.
Used in Chemical Synthesis:
Due to its unique structure, (2S)-4-(1,3-Dioxoisoindolin-2-yl)-2-hydroxybutanoic acid can be utilized as a building block in the synthesis of various complex organic molecules. Its reactivity and functional groups make it a valuable component in the development of new pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Research and Development:
(2S)-4-(1,3-Dioxoisoindolin-2-yl)-2-hydroxybutanoic acid's distinctive properties also make it an interesting subject for research and development in the fields of organic chemistry and medicinal chemistry. Scientists and researchers can explore its potential applications in the design of new drugs, materials, and other advanced technologies.

InChI:InChI=1/C12H11NO5/c14-9(12(17)18)5-6-13-10(15)7-3-1-2-4-8(7)11(13)16/h1-4,9,14H,5-6H2,(H,17,18)/p-1/t9-/m0/s1

Upstream product

• 85-44-9 phthalic anhydride 
• 3938-83-8 (S)-4-amino-2-hydroxybutanoic acid 

Downstream Products

• 1218922-63-4 (S)-benzyl 4-(1,3-dioxoisoindolin-2-yl)-2-hydroxybutanoate 

Relevant articles and documents

Synthesis method of amikacin intermediate

The invention belongs to the field of medicine synthesis, and particularly relates to a synthesis method of an amikacin intermediate. Phthaloyl chloride and 2-hydroxy-4-aminobutyric acid serve as theinitial raw materials, an acid-binding agent and a catalyst are added, the process of heating, washing, recrystallizing and the like is adopted, and finally the target amikacin intermediate product (2-hydroxy-4-phthaloyl iminobutyric acid) is obtained. In the synthesis method, the raw materials are easy to obtain, less reagents participate in the reaction, the steps are simple, operation is convenient, reaction conditions are mind, the product yield is high, and the method is suitable for industrial large-scale production.

A method for improving the yield of the method of preparing the amikacin

The invention discloses a method for increasing yield of amikacin. The method for increasing yield of amikacin comprises the following steps: heating, refluxing and carrying out reaction on gamma-amino-alpha-hydroxybutyric acid and fluorenylmethyl chloroformate, so as to generate a reaction liquid containing gamma-amino-alpha-hydroxybutyric acid; directly adding N-hydroxyl phthalimide and N,N-dicyclohexylcarbodiimide into the reaction liquid, and carrying out reaction to generate a reaction liquid containing active ester; directly adding a kanamycin A silanization compound into the reaction liquid containing the active ester for carrying out acylation reaction, after complete reaction is finished, adding an HBr aqueous solution until the pH is adjusted to be 2-3, and carrying out suction filtration to remove solid impurities; and then carrying out reduced pressure distillation for removing the solvent, adjusting the pH to be 7-8 with concentrated liquor, purifying by virtue of a CD180 macroporous resin column, concentrating, and carrying out freeze drying, so that amikacin solid is obtained. The active ester causes selectivity of the acylation reaction to be greatly improved due to enlargement of a protective group, and a follow-up processing step is also greatly simplified, so that the amikacin synthesis yield is increased.

DNA sequence selectivity of hairpin polyamide turn units

A class of hairpin polyamides linked by 3,4-diaminobutyric acid, resulting in a β-amine residue at the turn unit, showed improved binding affinities relative to their α-amino-γ-turn analogs for particular sequences. We incorporated β-amino-γ-turns in six-