N-[3-Fluoro-4-[(methylamino)carbonyl]phenyl]-2-methylalanine methyl ester

Base Information

• Chemical Name: N-[3-Fluoro-4-[(methylamino)carbonyl]phenyl]-2-methylalanine methyl ester
• CAS No.: 1332524-01-2
• Molecular Formula: C13H17FN2O3
• Molecular Weight: 268.288
• Mol file: 1332524-01-2.mol

Synonyms:N-[3-Fluoro-4-[(methylamino)carbonyl]phenyl]-2-methylalanine methyl ester;Alanine, N-[3-fluoro-4-[(MethylaMino)carbonyl]phenyl]-2-Methyl-, Methyl ester;Methyl 2-((3-fluoro-4-(MethylcarbaMoyl)phenyl)aMino)-2-Methylpropanoate;N-[3-fluoro-4-[(MethylaMino)carbonyl]phenyl]-2-Methyl-Alanine Methyl ester 2-(3-Fluoro-4-MethylcarbaMoyl-phenylaMino)-2-Methyl-propionic acid Methyl ester ";2-((3-fluoro-4-(methylcarbamoyl)phenyl)amino)-2-methylpropanoate methyl

Chemical Property of N-[3-Fluoro-4-[(methylamino)carbonyl]phenyl]-2-methylalanine methyl ester

Chemical Property:

• Boiling Point: 381℃
• PKA: 14.35±0.46(Predicted)
• Flash Point: 184℃
• PSA: 70.92000
• Density: 1.203
• LogP: 2.19660
• Solubility.: Chloroform, DCM, Ethyl Acetate

Purity/Quality:

N-[3-Fluoro-4-[(methylamino)carbonyl]phenyl]-2-methylalanineMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N-[3-Fluoro-4-[(methylamino)carbonyl]phenyl]-2-methylalanine Methyl Ester is an intermediate in the synthesis of MDV 3100 (M199800), is an androgen-receptor antagonist that blocks androgens from binding to the androgen receptor and prevents nuclear translocation and co-activator recruitment of the ligand-receptor complex.

Technology Process of N-[3-Fluoro-4-[(methylamino)carbonyl]phenyl]-2-methylalanine methyl ester

There total 5 articles about N-[3-Fluoro-4-[(methylamino)carbonyl]phenyl]-2-methylalanine methyl 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: 95.0%

2-((3-fluoro-4-(methylcarbamoyl)phenyl)amino)-2-methyl propanoic acid (1289942-66-0) + methyl iodide (74-88-4) → 2-(3-fluoro-4-(methylcarbamoyl)phenylamino)-2-methylpropanoic acid methyl ester (1332524-01-2)

Guidance literature:

2-((3-fluoro-4-(methylcarbamoyl)phenyl)amino)-2-methyl propanoic acid; With potassium carbonate; In water; N,N-dimethyl-formamide; at 30 ℃;

methyl iodide; In water; N,N-dimethyl-formamide; at 32 - 40 ℃; for 1.08333h;

Reference yield: 90.0%

methanol (67-56-1) + 2-((3-fluoro-4-(methylcarbamoyl)phenyl)amino)-2-methyl propanoic acid (1289942-66-0) → 2-(3-fluoro-4-(methylcarbamoyl)phenylamino)-2-methylpropanoic acid methyl ester (1332524-01-2)

Guidance literature:

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In N,N-dimethyl-formamide; at 0 - 30 ℃; for 8h; Inert atmosphere;

Reference yield:

2-fluoro-4-bromobenzoic acid (112704-79-7) → 2-(3-fluoro-4-(methylcarbamoyl)phenylamino)-2-methylpropanoic acid methyl ester (1332524-01-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: thionyl chloride / N,N-dimethyl-formamide; Isopropyl acetate / 4.58 h / 21 - 72 °C / Inert atmosphere; Industry scale

2.1: water; Isopropyl acetate / 1.08 h / 2 - 35 °C / Inert atmosphere; Industry scale

3.1: potassium carbonate / copper(l) chloride / N,N-dimethyl-formamide; water / 30 °C

3.2: 105 °C / Inert atmosphere

3.3: pH 4

4.1: potassium carbonate / N,N-dimethyl-formamide; water / 30 °C

4.2: 1.08 h / 32 - 40 °C

With thionyl chloride; potassium carbonate; copper(l) chloride; In Isopropyl acetate; water; N,N-dimethyl-formamide;

upstream raw materials:

2-((3-fluoro-4-(methylcarbamoyl)phenyl)amino)-2-methyl propanoic acid

methyl iodide

2-fluoro-4-bromobenzoic acid

4-bromo-2-fluorobenzoyl chloride

Downstream raw materials:

enzalutamide

4-(3-(4-cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo-2-imidazolidinethione-1-yl)-2-fluorobenzoic acid

Refernces

• 1、 Pertusati, Fabrizio,Ferla, Salvatore,Bassetto, Marcella,Brancale, Andrea,Khandil,Westwell, Andrew D.,McGuigan, Christopher. "A new series of bicalutamide, enzalutamide and enobosarm derivatives carrying pentafluorosulfanyl (SF5) and pentafluoroethyl (C2F5) substituents: Improved antiproliferative agents against prostate cancer". . p. 1 - 14. Retrieved 2019/07/10.
• 2、 -. "A "one-pot synthesis" method of synthesizing graciousness mixed Lu An". Paragraph 0029-0033. . Retrieved 2017/03/14.