(R)-aminoglutethimide

Base Information

• Chemical Name: (R)-aminoglutethimide
• CAS No.: 55511-44-9
• Molecular Formula: C13H16N2O2
• Molecular Weight: 232.282
• European Community (EC) Number: 623-492-4
• UNII: LUC985IS6T
• DSSTox Substance ID: DTXSID501318980
• Nikkaji Number: J231.950K
• Wikidata: Q27124213
• Metabolomics Workbench ID: 58760
• ChEMBL ID: CHEMBL2051951
• Mol file: 55511-44-9.mol

Synonyms:D-AG enantiomer;dexaminoglutethimide;L-AG enantiomer

Chemical Property of (R)-aminoglutethimide

Chemical Property:

• Vapor Pressure: 1.5E-08mmHg at 25°C
• Melting Point: 115.5-119.5oC(lit.)
• Boiling Point: 457.4°Cat760mmHg
• PKA: 11.60±0.40(Predicted)
• Flash Point: 230.4°C
• PSA: 72.19000
• Density: 1.173g/cm³
• LogP: 1.73730
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 232.121177757
• Heavy Atom Count: 17
• Complexity: 321

Purity/Quality:

98%,99%, ^*data from raw suppliers

(R)-(+)-Aminoglutethimide 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC1(CCC(=O)NC1=O)C2=CC=C(C=C2)N
• Isomeric SMILES: CC[C@@]1(CCC(=O)NC1=O)C2=CC=C(C=C2)N
• Uses: (R)-(+)-Aminoglutethimide can be used: As a building block for the development of cephalosporin based prodrug for antibody-directed enzyme prodrug therapy (ADEPT).To prepare (R)-3-ethyl-3-(4-(3,4,5-trimethoxybenzylamino)phenyl)piperidine-2,6-dione by reacting with 3,4,5-trimethoxybenzylamine via deaminative coupling reaction. To synthesize (R)-2-fluoro-2-(4-methoxyphenyl)-N-(R)-(+)-aminoglutethimide by enantioselective α-fluorination.

Technology Process of (R)-aminoglutethimide

There total 20 articles about (R)-aminoglutethimide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

aminoglutethimide (125-84-8) → (+)404-3-(4-aminophenyl)-3-ethyl-2,6-piperidinedione (55511-44-9) + (-)-3-(4-aminophenyl)-3-ethylpiperidine-2,6-dione (57288-03-6)

Guidance literature:

With Chiral Pack IA; In tetrahydrofuran; hexane; at 25 ℃; Product distribution / selectivity; Resolution of racemate;

Reference yield:

(R)-Diethyl 2-phenyl-2-ethylglutarate (170450-72-3) → (+)404-3-(4-aminophenyl)-3-ethyl-2,6-piperidinedione (55511-44-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 89 percent / aq. NaOH / ethanol / 4 h / Heating

2: 81 percent / 30percent NH₃ / 1 h / 180 - 200 °C

3: 85 percent / 63percent HNO₃, conc. H₂SO₄ / -10 °C

4: 94 percent / H₂ / 5percent Pd/C / ethanol

With ammonium hydroxide; sodium hydroxide; sulfuric acid; hydrogen; nitric acid; palladium on activated charcoal; In ethanol;

DOI:10.1021/jo00122a064

Reference yield:

(S)-Diethyl 2-phenyl-2-formylglutarate (170450-70-1) → (+)404-3-(4-aminophenyl)-3-ethyl-2,6-piperidinedione (55511-44-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 61 percent / Me₃Al, Zn / tetrahydrofuran; hexane / 1 h / 0 °C

2: 95 percent / H₂ / 5percent Pd/C / ethanol

3: 89 percent / aq. NaOH / ethanol / 4 h / Heating

4: 81 percent / 30percent NH₃ / 1 h / 180 - 200 °C

5: 85 percent / 63percent HNO₃, conc. H₂SO₄ / -10 °C

6: 94 percent / H₂ / 5percent Pd/C / ethanol

With ammonium hydroxide; sodium hydroxide; sulfuric acid; hydrogen; trimethylaluminum; nitric acid; zinc; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane;

DOI:10.1021/jo00122a064

upstream raw materials:

aminoglutethimide

4,5-Dioxo-3-phenyl-tetrahydro-furan-3-carboxylic acid ethyl ester

(R)-2-Phenyl-2-ethylglutaric acid

(R)-Diethyl 2-phenyl-2-vinylglutarate

Downstream raw materials:

(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

C₂₂H₂₃FN₂O₄