Diethyl 2-acetamido-2-[2-(4-octylphenyl)-2-oxoethyl]propanedioate

Base Information

• Chemical Name: Diethyl 2-acetamido-2-[2-(4-octylphenyl)-2-oxoethyl]propanedioate
• CAS No.: 268557-49-9
• Molecular Formula: C25H37NO6
• Molecular Weight: 447.572
• European Community (EC) Number: 813-247-1
• Nikkaji Number: J1.342.325C
• Mol file: 268557-49-9.mol

Synonyms:268557-49-9;diethyl 2-acetamido-2-[2-(4-octylphenyl)-2-oxoethyl]propanedioate;2-(Acetylamino)-2-[2-(4-octylphenyl)-2-oxoethyl]-propanedioic acid 1,3-diethyl ester;SCHEMBL5847172;FXWGCWKFKYSSLD-UHFFFAOYSA-N;[2-(4-Octylphenyl)-2-oxoethyl](acetylamino)malonic acid diethyl ester

Chemical Property of Diethyl 2-acetamido-2-[2-(4-octylphenyl)-2-oxoethyl]propanedioate

Chemical Property:

• Boiling Point: 607.6±55.0 °C(Predicted)
• PKA: 11.50±0.46(Predicted)
• PSA: 98.77000
• Density: 1.080±0.06 g/cm3 (20 oC 760 Torr)
• LogP: 4.55440
• XLogP3: 5.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 17
• Exact Mass: 447.26208790
• Heavy Atom Count: 32
• Complexity: 592

Purity/Quality:

98%min ^*data from raw suppliers

Diethyl2-Acetamido-2-[2-(4-octylphenyl)-2-oxo-ethyl]malonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCC1=CC=C(C=C1)C(=O)CC(C(=O)OCC)(C(=O)OCC)NC(=O)C
• Uses: Diethyl 2-Acetamido-2-[2-(4-octylphenyl)-2-oxo-ethyl]malonate is a reactant that has been used in the preparation of the immunosuppressive agent FRY-720 (F805000).

Technology Process of Diethyl 2-acetamido-2-[2-(4-octylphenyl)-2-oxoethyl]propanedioate

There total 9 articles about Diethyl 2-acetamido-2-[2-(4-octylphenyl)-2-oxoethyl]propanedioate 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: 94.0%

α-bromomethyl p(n-octyl)phenyl cetone (64068-76-4) + 2-acetylaminomalonic acid diethyl ester (1068-90-2) → 2-(acetylamino)-2-[2-(4-octylphenyl)-2-oxo-ethyl]propanedioic acid diethyl ester (268557-49-9)

Guidance literature:

With caesium carbonate; In acetonitrile; for 4h; Reflux;

Reference yield:

Octylbenzene (2189-60-8) → 2-(acetylamino)-2-[2-(4-octylphenyl)-2-oxo-ethyl]propanedioic acid diethyl ester (268557-49-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: AlCl₃

2.1: NaOEt / ethanol / 1 h / 60 °C

2.2: 90 percent / ethanol / 1 h / 60 °C

With aluminium trichloride; sodium ethanolate; In ethanol; 1.1: Friedel-Crafts acylation;

DOI:10.1016/j.bmcl.2005.07.057

Reference yield:

α-bromomethyl p(n-octyl)phenyl cetone (64068-76-4) + sodium ethanolate (141-52-6) + 2-acetylaminomalonic acid diethyl ester (1068-90-2) → 2-(acetylamino)-2-[2-(4-octylphenyl)-2-oxo-ethyl]propanedioic acid diethyl ester (268557-49-9)

Guidance literature:

In ethanol; hexane;

upstream raw materials:

α-bromomethyl p(n-octyl)phenyl cetone

2-acetylaminomalonic acid diethyl ester

Octylbenzene

sodium ethanolate

Downstream raw materials:

N-(1-hydroxy-2-(hydroxymethyl)-4-(4-octylphenyl) butan-2-yl) acetamide

fingolimod

3-amino-3-(hydroxymethyl)-1-(4-octylphenyl)butane-1,4-diol

N-[1,1-bis(hydroxymethyl)-3chloro-(4-octylphenyl)propyl]acetamide

Refernces

• 1、 -. "NEW LIGANDS FOR TARGETING OF S1P RECEPTORS FOR IN VIVO IMAGING AND TREATMENT OF DISEASES". Paragraph 0486; 0487; 0488; 0489. . Retrieved 2014/06/25.
• 2、 -. "NEW LIGANDS FOR TARGETING OF S1P RECEPTORS FOR IN VIVO IMAGING AND TREATMENT OF DISEASES". Page/Page column 63-64. . Retrieved 2013/03/26.