(1S,2S,3S)-1-chloro-N-hydroxy-2-(4-(5-methylpyrimidin-2-yl)phenyl)-3-phenylcyclopropanecarboxamide

Base Information

• Chemical Name: (1S,2S,3S)-1-chloro-N-hydroxy-2-(4-(5-methylpyrimidin-2-yl)phenyl)-3-phenylcyclopropanecarboxamide
• CAS No.: 1544495-48-8
• Molecular Formula: C₂₁H₁₈ClN₃O₂
• Molecular Weight: 379.846
• Mol file: 1544495-48-8.mol

Synonyms:

Chemical Property of (1S,2S,3S)-1-chloro-N-hydroxy-2-(4-(5-methylpyrimidin-2-yl)phenyl)-3-phenylcyclopropanecarboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,3S)-1-chloro-N-hydroxy-2-(4-(5-methylpyrimidin-2-yl)phenyl)-3-phenylcyclopropanecarboxamide

There total 9 articles about (1S,2S,3S)-1-chloro-N-hydroxy-2-(4-(5-methylpyrimidin-2-yl)phenyl)-3-phenylcyclopropanecarboxamide 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-chloro-2-phenyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclopropanecarboxylate → (1S,2S,3S)-1-chloro-N-hydroxy-2-(4-(5-methylpyrimidin-2-yl)phenyl)-3-phenylcyclopropanecarboxamide (1544495-48-8)

Guidance literature:

Multi-step reaction with 3 steps

1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium fluoride / 1,4-dioxane / 17 h / Inert atmosphere; Heating

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; cesium fluoride; potassium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; formic acid; n-heptane; isopropyl alcohol; 1: |Suzuki Coupling;

DOI:10.1021/acsmedchemlett.5b00302

Reference yield:

(1SR,2SR,3SR)-methyl 1-chloro-2-(4-(5-methylpyrimidin-2-yl)phenyl)-3-phenylcyclopropanecarboxylate → (1S,2S,3S)-1-chloro-N-hydroxy-2-(4-(5-methylpyrimidin-2-yl)phenyl)-3-phenylcyclopropanecarboxamide (1544495-48-8)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With hydroxylamine; potassium hydroxide; In tetrahydrofuran; methanol; formic acid; n-heptane; isopropyl alcohol;

DOI:10.1021/acsmedchemlett.5b00302

Reference yield:

(1S*,2S*,3S*)-1-chloro-N-hydroxy-2-(4-(5-methylpyrimidin-2-yl)phenyl)-3-phenylcyclopropanecarboxamide → (1S,2S,3S)-1-chloro-N-hydroxy-2-(4-(5-methylpyrimidin-2-yl)phenyl)-3-phenylcyclopropanecarboxamide (1544495-48-8)

Guidance literature:

With Chiralpak IC; In methanol; formic acid; n-heptane; isopropyl alcohol; Resolution of racemate;

DOI:10.1021/acsmedchemlett.5b00302

upstream raw materials:

methyl (E)-4-bromocinnamate

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