(Rs)-2-methyl-N-((S)-1-(2-(phenylethynyl)-5-(trifluoromethyl)phenyl)but-3-en-1-yl)propane-2-sulfinamide

Base Information

• Chemical Name: (Rs)-2-methyl-N-((S)-1-(2-(phenylethynyl)-5-(trifluoromethyl)phenyl)but-3-en-1-yl)propane-2-sulfinamide
• CAS No.: 1560811-30-4
• Molecular Formula: C₂₃H₂₄F₃NOS
• Molecular Weight: 419.511
• Mol file: 1560811-30-4.mol

Synonyms:(Rs)-2-methyl-N-((S)-1-(2-(phenylethynyl)-5-(trifluoromethyl)phenyl)but-3-en-1-yl)propane-2-sulfinamide

Chemical Property of (Rs)-2-methyl-N-((S)-1-(2-(phenylethynyl)-5-(trifluoromethyl)phenyl)but-3-en-1-yl)propane-2-sulfinamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Rs)-2-methyl-N-((S)-1-(2-(phenylethynyl)-5-(trifluoromethyl)phenyl)but-3-en-1-yl)propane-2-sulfinamide

There total 2 articles about (Rs)-2-methyl-N-((S)-1-(2-(phenylethynyl)-5-(trifluoromethyl)phenyl)but-3-en-1-yl)propane-2-sulfinamide 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: 70.0%

(Rs)-N-((S)-1-(2-iodo-5-(trifluoromethyl)phenyl)but-3-en-1-yl)-2-methylpropane-2-sulfinamide (1560811-12-2) + phenylacetylene (536-74-3) → (Rs)-2-methyl-N-((S)-1-(2-(phenylethynyl)-5-(trifluoromethyl)phenyl)but-3-en-1-yl)propane-2-sulfinamide (1560811-30-4)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In tetrahydrofuran; triethylamine; at 65 ℃; for 6h; Inert atmosphere;

DOI:10.1021/ol500142c

Reference yield:

2-iodo-5-(trifluoromethyl)benzaldehyde (875446-23-4) → (Rs)-2-methyl-N-((S)-1-(2-(phenylethynyl)-5-(trifluoromethyl)phenyl)but-3-en-1-yl)propane-2-sulfinamide (1560811-30-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: titanium(IV) tetraethanolate / dichloromethane / 12 h / 20 °C / Inert atmosphere

1.2: 3 h / -60 °C / Inert atmosphere

2.1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / tetrahydrofuran; triethylamine / 6 h / 65 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; titanium(IV) tetraethanolate; copper(l) iodide; In tetrahydrofuran; dichloromethane; triethylamine; 2.1: |Sonogashira Cross-Coupling;

DOI:10.1021/ol500142c

Reference yield:

dicobalt octacarbonyl (15226-74-1,61091-28-9,61117-58-6) + (Rs)-2-methyl-N-((S)-1-(2-(phenylethynyl)-5-(trifluoromethyl)phenyl)but-3-en-1-yl)propane-2-sulfinamide (1560811-30-4) → (Rs)-2-methyl-N-((3aR,5S)-2-oxo-1-phenyl-7-(trifluoromethyl)-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-5-yl)propane-2-sulfinamide (1560811-67-7) + C24H24F3NO2S (1560811-70-2)

Guidance literature:

dicobalt octacarbonyl; (Rs)-2-methyl-N-((S)-1-(2-(phenylethynyl)-5-(trifluoromethyl)phenyl)but-3-en-1-yl)propane-2-sulfinamide; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere;

With 4-methylmorpholine N-oxide; In dichloromethane; at 20 ℃; for 12h; Overall yield = 80 %; Inert atmosphere;

DOI:10.1021/ol500142c

upstream raw materials:

2-iodo-5-(trifluoromethyl)benzaldehyde

(Rs)-N-((S)-1-(2-iodo-5-(trifluoromethyl)phenyl)but-3-en-1-yl)-2-methylpropane-2-sulfinamide

phenylacetylene

Downstream raw materials:

(Rs)-2-methyl-N-((3aR,5S)-2-oxo-1-phenyl-7-(trifluoromethyl)-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-5-yl)propane-2-sulfinamide

C₂₄H₂₄F₃NO₂S