N-[3-[1-(2-hydroxy-4-oxo-6-phenethyl-6-propyl-5H-pyran-3-yl)propyl]phenyl]-5-(trifluoromethyl)pyridine-2-sulfonamide

Base Information

• Chemical Name: N-[3-[1-(2-hydroxy-4-oxo-6-phenethyl-6-propyl-5H-pyran-3-yl)propyl]phenyl]-5-(trifluoromethyl)pyridine-2-sulfonamide
• CAS No.: 174484-81-2
• Molecular Formula: C₃₁H₃₃F₃N₂O₅S
• Molecular Weight: 602.675
• Mol file: 174484-81-2.mol

Synonyms:N-[3-[1-(2-hydroxy-4-oxo-6-phenethyl-6-propyl-5H-pyran-3-yl)propyl]phenyl]-5-(trifluoromethyl)pyridine-2-sulfonamide

Chemical Property of N-[3-[1-(2-hydroxy-4-oxo-6-phenethyl-6-propyl-5H-pyran-3-yl)propyl]phenyl]-5-(trifluoromethyl)pyridine-2-sulfonamide

Chemical Property:

• Vapor Pressure: 2.01E-19mmHg at 25°C
• Boiling Point: 680°Cat760mmHg
• Flash Point: 365.1°C
• PSA: 113.97000
• Density: 1.313g/cm³
• LogP: 8.47930

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-[3-[1-(2-hydroxy-4-oxo-6-phenethyl-6-propyl-5H-pyran-3-yl)propyl]phenyl]-5-(trifluoromethyl)pyridine-2-sulfonamide

There total 47 articles about N-[3-[1-(2-hydroxy-4-oxo-6-phenethyl-6-propyl-5H-pyran-3-yl)propyl]phenyl]-5-(trifluoromethyl)pyridine-2-sulfonamide 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: 81.0%

5-trifluoromethyl-pyridin-2-ylsulfonylchloride (174485-72-4) + (R)-3-[(R)-1-(3-Amino-phenyl)-propyl]-4-hydroxy-6-phenethyl-6-propyl-5,6-dihydro-pyran-2-one (174485-90-6) → tipranavir (174484-41-4,174484-81-2,174590-27-3)

Guidance literature:

With pyridine; In dichloromethane;

DOI:10.1021/ja963434w

Reference yield: 77.4%

(R)-3-[(R)-1-(3-Amino-phenyl)-propyl]-4-hydroxy-6-phenethyl-6-propyl-5,6-dihydro-pyran-2-one (174485-90-6) + 4-(trifluoromethyl)pyridine-2-sulfonyl chloride (174485-71-3) → tipranavir (174484-41-4,174484-81-2,174590-27-3)

Guidance literature:

In dichloromethane; dimethyl sulfoxide; at -30 - -25 ℃; for 2h;

DOI:10.1021/jo9809229

Reference yield:

(E)-pent-2-enoyl chloride (33698-85-0) → tipranavir (174484-41-4,174484-81-2,174590-27-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 95 percent / n-BuLi / tetrahydrofuran / -78 °C

2: CuBr, DMS / tetrahydrofuran / 1 h / 0 °C

3: 1.) H₃O⁺, 2.) Na₂CO₃ / 2.) H₂O, CH₂Cl₂

6: 67 percent / t-BuOK / tetrahydrofuran / 0 °C

7: H₂ / Pd/C / methanol; ethyl acetate

8: 81 percent / pyridine / CH₂Cl₂

With pyridine; n-butyllithium; 2,3-dimercapto-succinic acid; oxonium; potassium tert-butylate; hydrogen; sodium carbonate; copper(I) bromide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;

DOI:10.1021/ja963434w

upstream raw materials:

5-trifluoromethyl-pyridin-2-ylsulfonylchloride

(R)-3-[(R)-1-(3-Amino-phenyl)-propyl]-4-hydroxy-6-phenethyl-6-propyl-5,6-dihydro-pyran-2-one

4-(trifluoromethyl)pyridine-2-sulfonyl chloride

1-phenylhexan-3-one