55511-44-9

Basic information

• Product Name: (R)-(+)-AMINOGLUTETHIMIDE 97
• Synonyms: (R)-(+)-AMINOGLUTETHIMIDE 97;(R)-3-(4-Aminophenyl)-3-ethyl-2,6-piperidinedione;CGS-2396;2,6-Piperidinedione, 3-(4-aminophenyl)-3-ethyl-, (3R)-;Aminoglutethimide, D-;(R)-3-(4-aMinophenyl)-3-ethylpiperidine-2,6-dione;(R)-(+)-Aminoglutethimide 97%
• CAS NO: 55511-44-9
• Molecular Formula: C₁₃H₁₆N₂O₂
• Molecular Weight: 232.28
• Product Categories: Chiral Building Blocks;Cyclic Imides;Organic Building Blocks
• Mol File: 55511-44-9.mol
• Article Data: 9

Chemical Properties

• Melting Point: 115.5-119.5 °C(lit.)
• Boiling Point: 457.4°Cat760mmHg
• Flash Point: 230.4°C
• Appearance: /
• Density: 1.173g/cm³
• Vapor Pressure: 1.5E-08mmHg at 25°C
• Refractive Index: 1.566
• PKA: 11.60±0.40(Predicted)
• CAS DataBase Reference: (R)-(+)-AMINOGLUTETHIMIDE 97(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-AMINOGLUTETHIMIDE 97(55511-44-9)
• EPA Substance Registry System: (R)-(+)-AMINOGLUTETHIMIDE 97(55511-44-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 55511-44-9(Hazardous Substances Data)

Usage

Description

(R)-(+)-Aminoglutethimide, also known as the (3R)-enantiomer of aminoglutethimide, is an organic compound with a specific stereochemistry. It is a chiral molecule, which means it has a non-superimposable mirror image, and the (R)-(+)-enantiomer is the biologically active form. (R)-(+)-AMINOGLUTETHIMIDE 97 has been found to have various applications in the pharmaceutical and chemical industries due to its unique properties and reactivity.

Uses

Used in Pharmaceutical Industry:
(R)-(+)-Aminoglutethimide is used as a building block for the development of cephalosporin-based prodrugs for antibody-directed enzyme prodrug therapy (ADEPT). This application takes advantage of its reactivity and stereochemistry to create targeted therapies for specific conditions.
Used in Chemical Synthesis:
(R)-(+)-Aminoglutethimide is used as a starting material to prepare (R)-3-ethyl-3-(4-(3,4,5-trimethoxybenzylamino)phenyl)piperidine-2,6-dione by reacting with 3,4,5-trimethoxybenzylamine via a deaminative coupling reaction. This synthesis is important for the development of new compounds with potential pharmaceutical applications.
Used in Enantioselective Fluorination:
(R)-(+)-Aminoglutethimide is also used to synthesize (R)-2-fluoro-2-(4-methoxyphenyl)-N-(R)-(+)-aminoglutethimide through enantioselective α-fluorination. This process allows for the creation of chiral fluorinated compounds, which have potential applications in various fields, including pharmaceuticals and materials science.

InChI:InChI=1/C13H16N2O2/c1-2-13(8-7-11(16)15-12(13)17)9-3-5-10(14)6-4-9/h3-6H,2,7-8,14H2,1H3,(H,15,16,17)/t13-/m1/s1

Upstream product

• 125-84-8 aminoglutethimide 
• 170450-61-0 4,5-Dioxo-3-phenyl-tetrahydro-furan-3-carboxylic acid ethyl ester 
• 1027948-84-0 (R)-2-Phenyl-2-ethylglutaric acid 
• 170450-71-2 (R)-Diethyl 2-phenyl-2-vinylglutarate 
• 170450-72-3 (R)-Diethyl 2-phenyl-2-ethylglutarate 
• 170450-70-1 (S)-Diethyl 2-phenyl-2-formylglutarate 
• 170450-69-8 (S)-Diethyl 2-phenyl-2-(hydroxymethyl)glutarate 
• 170450-68-7 (S)-Diethyl 4-phenyl-4-<(formyloxy)methyl>glutaconate 
• 170450-66-5 (S)-Ethyl 2-formyl-2-<(formyloxy)methyl>phenylpropionate 
• 170450-62-1 (3S,4R)-4-Hydroxy-5-oxo-3-phenyl-tetrahydro-furan-3-carboxylic acid ethyl ester 
• 17575-58-5 glutethimide 
• 100-00-5 4-chlorobenzonitrile 
• 30698-33-0 methyl 2-cyano-2-(4-nitrophenyl)acetate 
• 94814-82-1 2-(4-nitrophenyl)butanonitrile 

Downstream Products

• 805231-43-0 (6R,7R)-7-Allyloxycarbonylamino-3-[4-((R)-3-ethyl-2,6-dioxo-piperidin-3-yl)-phenylcarbamoyloxymethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 
• 1205648-10-7 C₂₂H₂₃FN₂O₄ 

Relevant articles and documents

Colistin sulfate chiral stationary phase for the enantioselective separation of pharmaceuticals using organic polymer monolithic capillary chromatography ?

A new functionalized polymer monolithic capillary with a macrocyclic antibiotic, namely colistin sulfate, as chiral selector was prepared via the copolymerization of binary monomer mixtures consisting of glycidyl methacrylate (GMA) and ethylene glycol dimethacrylate (EGDMA) in porogenic solvents namely 1-propanol and 1,4-butanediol, in the presence of azobisiso-butyronitrile (AIBN) as initiator and colistin sulfate. The prepared capillaries were investigated for the enantioselective nano-LC separation of a group of racemic pharmaceuticals, namely, α- and β-blockers, anti-inflammatory drugs, antifungal drugs, norepinephrine-dopamine reuptake inhibitors, catecholamines, sedative hypnotics, antihistaminics, anticancer drugs, and antiarrhythmic drugs. Acceptable separation was achieved for many drugs using reversed phase chromatographic conditions with no separation achieved under normal phase conditions. Colistin sulfate appears to be useful addition to the available macrocyclic antibiotic chiral phases used in liquid chromatography.

Synthesis of dendrimer-type chiral stationary phases based on the selector of (1S,2R)-(+)-2-amino-1,2-diphenylethanol derivate and their enantioseparation evaluation by HPLC

In our recent work, a series of dendritic chiral stationary phases (CSPs) were synthesized, in which the chiral selector was L-2-(p-toluenesulfonamido)-3- phenylpropionyl chloride (selector I), and the CSP derived from three-generation dendrimer showed the best separation ability. To further investigate the influence of the structures of dendrimer and chiral selector on enantioseparation ability, in this work, another series CSPs (CSPs 1-4) were prepared by immobilizing (1S,2R)-1,2-diphenyl-2-(3-phenylureido)ethyl 4-isocyanatophenylcarbamate (selector II) on one- to four-generation dendrimers that were prepared in previous work. CSPs 1 and 4 demonstrated the equivalent enantioseparation ability. CSPs 2 and 3 showed the best and poorest enantioseparation ability respectively. Basically, these two series of CSPs exhibited the equivalent enantioseparation ability although the chiral selectors were different. Considering the enantioseparation ability of the CSP derived from aminated silica gel and selector II is much better than that of the one derived from aminated silica gel and selector I, it is believed that the dendrimer conformation essentially impacts enantioseparation.

Method of Analyzing Optical Isomers or Method of Resolving the Same

Provided are a method of quickly and simply confirming the success or failure of resolution of optical isomers with the use of a column for resolving optical isomers and a method of simply designing the conditions of the eluent composition under isocratic elution conditions. In resolving optical isomers, the success or failure of the resolution can be simply and quickly confirmed by employing an HPLC gradient elution analysis method with the use of a column for resolving optical isomers. When the resolution is successfully conducted, the eluent composition under isocratic elution conditions can be estimated from the elution time in the gradient elution analysis.