Diethyl acetamido[(4-bromophenyl)methyl]propanedioate

Base Information

• Chemical Name: Diethyl acetamido[(4-bromophenyl)methyl]propanedioate
• CAS No.: 71078-92-7
• Molecular Formula: C16H20BrNO5
• Molecular Weight: 386.243
• DSSTox Substance ID: DTXSID50551693
• Wikidata: Q82431492
• Mol file: 71078-92-7.mol

Synonyms:71078-92-7;Diethyl acetamido[(4-bromophenyl)methyl]propanedioate;SCHEMBL9849155;DTXSID50551693

Chemical Property of Diethyl acetamido[(4-bromophenyl)methyl]propanedioate

Chemical Property:

• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 385.05249
• Heavy Atom Count: 23
• Complexity: 414

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(CC1=CC=C(C=C1)Br)(C(=O)OCC)NC(=O)C

Technology Process of Diethyl acetamido[(4-bromophenyl)methyl]propanedioate

There total 3 articles about Diethyl acetamido[(4-bromophenyl)methyl]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: 79.0%

1-bromomethyl-4-bromobenzene (589-15-1) + 2-acetylaminomalonic acid diethyl ester (1068-90-2) → diethyl (acetylamino)<(4-bromophenyl)methyl>propanedioate (71078-92-7)

Guidance literature:

With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate; In acetonitrile; for 2h; Heating;

DOI:10.1016/S0040-4020(01)90076-6

Reference yield:

diethyl aminomalonate hydrochloride (13433-00-6) → diethyl (acetylamino)<(4-bromophenyl)methyl>propanedioate (71078-92-7)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / dichloromethane / 0 - 20 °C

2: caesium carbonate / acetonitrile / 130 °C / Microwave irradiation

With caesium carbonate; triethylamine; In dichloromethane; acetonitrile;

DOI:10.1021/acs.orglett.8b02791

Reference yield:

→ diethyl (acetylamino)<(4-bromophenyl)methyl>propanedioate (71078-92-7)

Guidance literature:

aus 4-Brombenzylbromid und Acetaminomalonsaeurediethylester, K2CO3;

upstream raw materials:

1-bromomethyl-4-bromobenzene

2-acetylaminomalonic acid diethyl ester

diethyl aminomalonate hydrochloride

Downstream raw materials:

4-bromophenylalanine-hydrochloride

ethyl 4-bromo-N-acetylphenylalaninate

diethyl (acetylamino)<<4-(diethoxyphosphinyl)phenyl>methyl>propanedioate

4-Phosphono-DL-phenylalanine