(1S,2S,3S)-1-fluoro-N-hydroxy-2-phenyl-3-(4-(4-(trifluoromethyl)pyrimidin-2-yl)phenyl)cyclopropanecarboxamide

Base Information

• Chemical Name: (1S,2S,3S)-1-fluoro-N-hydroxy-2-phenyl-3-(4-(4-(trifluoromethyl)pyrimidin-2-yl)phenyl)cyclopropanecarboxamide
• CAS No.: 1544496-24-3
• Molecular Formula: C₂₁H₁₅F₄N₃O₂
• Molecular Weight: 417.363
• Mol file: 1544496-24-3.mol

Synonyms:(1S,2S,3S)-1-fluoro-N-hydroxy-2-phenyl-3-(4-(4-(trifluoromethyl)pyrimidin-2-yl)phenyl)cyclopropanecarboxamide

Chemical Property of (1S,2S,3S)-1-fluoro-N-hydroxy-2-phenyl-3-(4-(4-(trifluoromethyl)pyrimidin-2-yl)phenyl)cyclopropanecarboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,3S)-1-fluoro-N-hydroxy-2-phenyl-3-(4-(4-(trifluoromethyl)pyrimidin-2-yl)phenyl)cyclopropanecarboxamide

There total 11 articles about (1S,2S,3S)-1-fluoro-N-hydroxy-2-phenyl-3-(4-(4-(trifluoromethyl)pyrimidin-2-yl)phenyl)cyclopropanecarboxamide 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:

(1SR,2SR,3SR)-methyl 1-fluoro-2-phenyl-3-(4-(4-(trifluoromethyl)pyrimidin-2-yl)phenyl)cyclopropanecarboxylate → (1S,2S,3S)-1-fluoro-N-hydroxy-2-phenyl-3-(4-(4-(trifluoromethyl)pyrimidin-2-yl)phenyl)cyclopropanecarboxamide (1544496-24-3) + (1R,2R,3R)-1-fluoro-N-hydroxy-2-phenyl-3-(4-(4-(trifluoromethyl)pyrimidin-2-yl)phenyl)cyclopropanecarboxamide (1544496-25-4)

Guidance literature:

With hydroxylamine; potassium hydroxide; In tetrahydrofuran; methanol; water; at 20 ℃; for 2h;

Reference yield:

methyl (1S*,2S*,3S*)-2-(4-bromophenyl)-1-fluoro-3-phenylcyclopropane-1-carboxylate → (1S,2S,3S)-1-fluoro-N-hydroxy-2-phenyl-3-(4-(4-(trifluoromethyl)pyrimidin-2-yl)phenyl)cyclopropanecarboxamide (1544496-24-3)

Guidance literature:

Multi-step reaction with 4 steps

1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 90 °C / Inert atmosphere

2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / 1,4-dioxane; water / 17 h / 100 °C / Inert atmosphere

3: hydroxylamine; potassium hydroxide / tetrahydrofuran; methanol / 20 °C

4: Chiralpak IC / methanol; isopropyl alcohol; formic acid; n-heptane / Resolution of racemate

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; hydroxylamine; potassium acetate; sodium carbonate; potassium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; formic acid; n-heptane; water; isopropyl alcohol; 2: |Suzuki Coupling;

DOI:10.1021/acsmedchemlett.5b00302

Reference yield:

(1SR,2SR,3SR)-methyl 1-fluoro-2-phenyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclopropanecarboxylate → (1S,2S,3S)-1-fluoro-N-hydroxy-2-phenyl-3-(4-(4-(trifluoromethyl)pyrimidin-2-yl)phenyl)cyclopropanecarboxamide (1544496-24-3)

Guidance literature:

Multi-step reaction with 3 steps

1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / 1,4-dioxane; water / 17 h / 100 °C / Inert atmosphere

2: hydroxylamine; potassium hydroxide / tetrahydrofuran; methanol / 20 °C

3: Chiralpak IC / methanol; isopropyl alcohol; formic acid; n-heptane / Resolution of racemate

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; hydroxylamine; sodium carbonate; potassium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; formic acid; n-heptane; water; isopropyl alcohol; 1: |Suzuki Coupling;

DOI:10.1021/acsmedchemlett.5b00302

upstream raw materials:

methyl (E)-4-bromocinnamate

2-bromo-4-(trifluoromethyl) pyrimidine

1-benzyltetrahydro-1H-thiophen-1-ium bromide