(2S)-3-BroMo-N-[4-cyano-3-(trifluoroMethyl)phenyl]-2-hydroxy-2-Methyl-propanaMide

Base Information

• Chemical Name: (2S)-3-BroMo-N-[4-cyano-3-(trifluoroMethyl)phenyl]-2-hydroxy-2-Methyl-propanaMide
• CAS No.: 113181-02-5
• Molecular Formula: C12H10BrF3N2O2
• Molecular Weight: 351.123
• Mol file: 113181-02-5.mol

Synonyms:(2S)-3-Bromo-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methyl-propanamide;

Chemical Property of (2S)-3-BroMo-N-[4-cyano-3-(trifluoroMethyl)phenyl]-2-hydroxy-2-Methyl-propanaMide

Chemical Property:

• Melting Point: >130°C (dec.)
• PSA: 73.12000
• LogP: 2.73448
• Storage Temp.: Refrigerator
• Solubility.: Acetone (Slightly), Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

99.90% ^*data from raw suppliers

(2S)-3-Bromo-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methyl-propanamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (2S)-3-Bromo-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methyl-propanamide is a reactant used in the preparation of hydroxy(phenylthio)propionanilides as affinity ligands for the androstane receptor.

Technology Process of (2S)-3-BroMo-N-[4-cyano-3-(trifluoroMethyl)phenyl]-2-hydroxy-2-Methyl-propanaMide

There total 4 articles about (2S)-3-BroMo-N-[4-cyano-3-(trifluoroMethyl)phenyl]-2-hydroxy-2-Methyl-propanaMide 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: 90.0%

4-amino-2-trifluoromethylbenzonitrile (654-70-6) + (S)-(-)-3-bromo-2-hydroxy-2-methylpropanoic acid (106089-20-7) → (S)-(-)-3-bromo-2-hydroxy-2-methyl-N-[(4-cyano-3-(trifluoromethyl)phenyl)]propanamide (113181-02-5)

Guidance literature:

With thionyl chloride; triethylamine;

Reference yield:

C4H6BrClO2 (1010729-05-1) + 4-amino-2-trifluoromethylbenzonitrile (654-70-6) → (S)-(-)-3-bromo-2-hydroxy-2-methyl-N-[(4-cyano-3-(trifluoromethyl)phenyl)]propanamide (113181-02-5)

Guidance literature:

In N,N-dimethyl acetamide; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.jorganchem.2010.10.051

Reference yield:

4-amino-2-trifluoromethylbenzonitrile (654-70-6) + 3-bromomethyl-3-methyl-tetrahydro-pyrrolo[2,1-c][1,4]oxazine-1,4-dione (927203-28-9) → (S)-(-)-3-bromo-2-hydroxy-2-methyl-N-[(4-cyano-3-(trifluoromethyl)phenyl)]propanamide (113181-02-5) + N1-[4-cyano-3-(trifluoromethyl)phenyl]-(2S)-3-chloro-2-hydroxy-2-methylpropanamide

Guidance literature:

3-bromomethyl-3-methyl-tetrahydro-pyrrolo[2,1-c][1,4]oxazine-1,4-dione; With hydrogenchloride; Heating;

With thionyl chloride; 2,4-dichlorophenoxyacetic acid dimethylamine; at -10 - -5 ℃;

4-amino-2-trifluoromethylbenzonitrile; With 2,4-dichlorophenoxyacetic acid dimethylamine; Further stages. Title compound not separated from byproducts.;

DOI:10.1021/jm990027x

upstream raw materials:

4-amino-2-trifluoromethylbenzonitrile

(S)-(-)-3-bromo-2-hydroxy-2-methylpropanoic acid

3-bromomethyl-3-methyl-tetrahydro-pyrrolo[2,1-c][1,4]oxazine-1,4-dione

C₄H₆BrClO₂

Downstream raw materials:

(R)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-methyloxirane-2-carboxamide

Refernces

• 1、 -. "SELECTIVE ANDROGEN RECEPTOR DEGRADER (SARD) LIGANDS AND METHODS OF USE THEREOF". Paragraph 00479-00481. . Retrieved 2019/12/04.
• 2、 Hwang, Dong-Jin,He, Yali,Ponnusamy, Suriyan,Mohler, Michael L.,Thiyagarajan, Thirumagal,McEwan, Iain J.,Narayanan, Ramesh,Miller, Duane D.. "New Generation of Selective Androgen Receptor Degraders: Our Initial Design, Synthesis, and Biological Evaluation of New Compounds with Enzalutamide-Resistant Prostate Cancer Activity". . p. 491 - 511. Retrieved 2019/01/11.