Propanedioic acid, (acetylamino)[(4-borono-2-fluorophenyl)methyl]-, 1,3-diethyl ester

Base Information

• Chemical Name: Propanedioic acid, (acetylamino)[(4-borono-2-fluorophenyl)methyl]-, 1,3-diethyl ester
• CAS No.: 292050-23-8
• Molecular Formula: C₁₆H₂₁BFNO₇
• Molecular Weight: 369.155
• DSSTox Substance ID: DTXSID001128140
• Mol file: 292050-23-8.mol

Synonyms:DTXSID001128140;Propanedioic acid, (acetylamino)[(4-borono-2-fluorophenyl)methyl]-, 1,3-diethyl ester;292050-23-8

Chemical Property of Propanedioic acid, (acetylamino)[(4-borono-2-fluorophenyl)methyl]-, 1,3-diethyl ester

Chemical Property:

• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 10
• Exact Mass: 369.1395103
• Heavy Atom Count: 26
• Complexity: 499

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: B(C1=CC(=C(C=C1)CC(C(=O)OCC)(C(=O)OCC)NC(=O)C)F)(O)O

Technology Process of Propanedioic acid, (acetylamino)[(4-borono-2-fluorophenyl)methyl]-, 1,3-diethyl ester

There total 3 articles about Propanedioic acid, (acetylamino)[(4-borono-2-fluorophenyl)methyl]-, 1,3-diethyl ester 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:

2-fluoro-4-bromotoluene (51436-99-8) → 2-[1-Acetylamino-2-(4-borono-2-fluorophenyl)ethyl]malonic acid diethyl ester (292050-23-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -50 °C

1.2: tetrahydrofuran; hexane / 12 h / 20 °C

1.3: 91 percent / aq. HCl / tetrahydrofuran; hexane

2.1: Br₂ / CCl₄ / Irradiation

3.1: NaOEt / ethanol / 0.75 h

3.2: 21.4 g / ethanol / 12 h / Heating

With n-butyllithium; bromine; sodium ethanolate; In tetrahydrofuran; tetrachloromethane; ethanol; hexane; 1.1: Metallation / 1.2: Substitution / 1.3: Hydrolysis / 2.1: Bromination / 3.1: Metallation / 3.2: Alkylation;

DOI:10.1080/00304940009355929

Reference yield:

(3-fluoro-4-methylphenyl)boronic acid (168267-99-0) → 2-[1-Acetylamino-2-(4-borono-2-fluorophenyl)ethyl]malonic acid diethyl ester (292050-23-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Br₂ / CCl₄ / Irradiation

2.1: NaOEt / ethanol / 0.75 h

2.2: 21.4 g / ethanol / 12 h / Heating

With bromine; sodium ethanolate; In tetrachloromethane; ethanol; 1.1: Bromination / 2.1: Metallation / 2.2: Alkylation;

DOI:10.1080/00304940009355929

Reference yield:

C7H7BBrFO2 + Diethyl acetamidomalonate → 2-[1-Acetylamino-2-(4-borono-2-fluorophenyl)ethyl]malonic acid diethyl ester (292050-23-8)

Guidance literature:

Diethyl acetamidomalonate; With sodium ethanolate; In ethanol; for 0.75h;

C₇H₇BBrFO₂; In ethanol; for 12h; Heating;

DOI:10.1080/00304940009355929

upstream raw materials:

2-fluoro-4-bromotoluene

(3-fluoro-4-methylphenyl)boronic acid