Diethyl (acetylamino)(4-fluorobenzyl)propanedioate

Base Information

• Chemical Name: Diethyl (acetylamino)(4-fluorobenzyl)propanedioate
• CAS No.: 380-71-2
• Molecular Formula: C16H20FNO5
• Molecular Weight: 325.337
• DSSTox Substance ID: DTXSID90369476
• Nikkaji Number: J2.491.210H
• Wikidata: Q82156572
• Mol file: 380-71-2.mol

Synonyms:380-71-2;diethyl (acetylamino)(4-fluorobenzyl)propanedioate;Maybridge1_006232;HMS559D06;DTXSID90369476;STK369241;AKOS000716411;Propanedioic acid, (acetylamino)[(4-fluorophenyl)methyl]-, diethyl ester;CCG-248549;BRD-K33419625-001-01-1;2-(4-Fluorobenzyl)-2-(acetylamino)malonic acid diethyl ester

Chemical Property of Diethyl (acetylamino)(4-fluorobenzyl)propanedioate

Chemical Property:

• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 325.13255090
• Heavy Atom Count: 23
• Complexity: 414

Purity/Quality:

95% ^*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)F)(C(=O)OCC)NC(=O)C

Technology Process of Diethyl (acetylamino)(4-fluorobenzyl)propanedioate

There total 6 articles about Diethyl (acetylamino)(4-fluorobenzyl)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: 99.0%

4-Fluorobenzyl bromide (459-46-1) + 2-acetylaminomalonic acid diethyl ester (1068-90-2) → diethyl α-acetamido, α-(4-fluorobenzyl)malonate (380-71-2)

Guidance literature:

With potassium carbonate; In acetonitrile; Heating;

Reference yield: 90.0%

p-fluorobenzyl acetate (502-00-1) + 2-acetylaminomalonic acid diethyl ester (1068-90-2) → diethyl α-acetamido, α-(4-fluorobenzyl)malonate (380-71-2)

Guidance literature:

With 1,1'-bis-(diphenylphosphino)ferrocene; potassium carbonate; {(η4-1,5-cyclooctadiene)Pd(η3-allyl)}BF4; In tert-Amyl alcohol; at 80 ℃; for 24h;

DOI:10.1016/j.tetlet.2007.06.157

Reference yield:

diethyl aminomalonate hydrochloride (13433-00-6) → diethyl α-acetamido, α-(4-fluorobenzyl)malonate (380-71-2)

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

upstream raw materials:

4-Fluorobenzyl bromide

2-acetylaminomalonic acid diethyl ester

p-fluorobenzyl acetate

diethyl malonate

Downstream raw materials:

N-acetyl-4-fluoro-L-phenylalanine-(N'-phenyl-hydrazide)

(R)-N-acetyl-p-fluorophenylalanine

(R)-4-fluorophenylalanine

rac-Ac-p-F-Phe-OH

Refernces

• 1、 Yokogi, Masashi,Kuwano, Ryoichi. "Use of acetate as a leaving group in palladium-catalyzed nucleophilic substitution of benzylic esters". . p. 6109 - 6112. Retrieved 2008/03/12.
• 2、 Bram,Galons,Combet Farnoux,Miocque. "Efficient synthesis of alkylacetamidomalonates by solid-liquid phasetransfer catalysis without solvent". . p. 199 - 199. Retrieved 2007/10/02.