S-3-(4-Fluorophenoxy)-2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide

Base Information

• Chemical Name: S-3-(4-Fluorophenoxy)-2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide
• CAS No.: 401900-41-2
• Molecular Formula: C17H14F4N2O5
• Molecular Weight: 402.3
• DSSTox Substance ID: DTXSID501119697
• Nikkaji Number: J2.012.586A
• Wikidata: Q27096988
• Pharos Ligand ID: NFHA1J5BB337
• Metabolomics Workbench ID: 150929
• ChEMBL ID: CHEMBL124718
• Mol file: 401900-41-2.mol

Synonyms:S-3-(4-FLUOROPHENOXY)-2-HYDROXY-2-METHYL-N-[4-NITRO-3-(TRIFLUOROMETHYL)PHENYL]PROPANAMIDE;(2S)-3-(4-fluorophenoxy)-2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide;401900-41-2;CHEMBL124718;FHM;Nonsteroidal AR Ligand, S-5;SCHEMBL2746561;BDBM18663;DTXSID501119697;BMC185567 S-1;DB07769;PD005481;LS-192457;Q27096988;(2S)-N-[3-(Trifluoromethyl)-4-nitrophenyl]-2-hydroxy-2-methyl-3-(4-fluorophenoxy)propanamide;(S)-3-(4-Fluorophenoxy)-2-hydroxy-2-methyl-N-(4-nitro-3-trifluoromethylphenyl)propionamide, analytical standard

Chemical Property of S-3-(4-Fluorophenoxy)-2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide

Chemical Property:

• PSA: 104.38000
• LogP: 4.11740
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 5
• Exact Mass: 402.08388420
• Heavy Atom Count: 28
• Complexity: 563

Purity/Quality:

98%Min ^*data from raw suppliers

4-Desacetamido-4-fluoroAndarine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(COC1=CC=C(C=C1)F)(C(=O)NC2=CC(=C(C=C2)[N+](=O)[O-])C(F)(F)F)O
• Isomeric SMILES: C[C@](COC1=CC=C(C=C1)F)(C(=O)NC2=CC(=C(C=C2)[N+](=O)[O-])C(F)(F)F)O
• Uses: 4-Desacetamido-4-fluoro Andarine is a Selective Androgen Receptor Modulator (SARM) that has potential use for treatment of androgen related diseases such as muscle wasting and osteoporosis. 4-Desacetamido-4-fluoro Andarine is also a derivative of Andarine (A637470), a non-steroidal SARM that is used by athletes to enhance performance.

Technology Process of S-3-(4-Fluorophenoxy)-2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide

There total 6 articles about S-3-(4-Fluorophenoxy)-2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]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: 43.0%

4-Fluorophenol (371-41-5) + N-[4-nitro-3-(trifluoromethyl)phenyl]-(2R)-3-bromo-2-hydroxy-2-methylpropanamide (206193-18-2) → 3-(4-fluoro-phenoxy)-2-hydroxy-2-methyl-N-(4-nitro-3-trifluoromethyl-phenyl)-propionamide (401900-41-2,401900-44-5)

Guidance literature:

With benzyltri(n-butyl)ammonium chloride; potassium carbonate; In butanone; for 24h; Heating;

DOI:10.1021/jm030336u

Reference yield: 32.0%

4-Fluorophenol (371-41-5) + (S)-(-)-3-bromo-2-hydroxy-2-methyl-N-[(4-nitro-3-trifluoromethyl)phenyl]propanamide (216665-24-6) → 3-(4-fluoro-phenoxy)-2-hydroxy-2-methyl-N-(4-nitro-3-trifluoromethyl-phenyl)-propionamide (401900-41-2,401900-44-5)

Guidance literature:

With benzyltri(n-butyl)ammonium chloride; potassium carbonate; In butanone; for 24h; Heating;

DOI:10.1021/jm030336u

Reference yield:

N-[4-nitro-3-(trifluoromethyl)phenyl]-(2R)-3-bromo-2-hydroxy-2-methylpropanamide (206193-18-2) → 3-(4-fluoro-phenoxy)-2-hydroxy-2-methyl-N-(4-nitro-3-trifluoromethyl-phenyl)-propionamide (401900-41-2,401900-44-5)

Guidance literature:

Multi-step reaction with 2 steps

1: K₂CO₃ / acetone / Heating

2: K₂CO₃ / propan-2-ol / Heating

With potassium carbonate; In isopropyl alcohol; acetone;

DOI:10.1021/jm030336u

upstream raw materials:

4-Fluorophenol

(S)-(-)-3-bromo-2-hydroxy-2-methyl-N-[(4-nitro-3-trifluoromethyl)phenyl]propanamide

(S)-N-(4-nitro-3-(trifluoromethyl)phenyl)-2-methyloxirane-2-carboxamide

N-[4-nitro-3-(trifluoromethyl)phenyl]-(2R)-3-bromo-2-hydroxy-2-methylpropanamide

Refernces

• 1、 -. "Selective androgen receptor modulators and methods of use thereof". Page 17. . Retrieved 2008/06/13.