(R)-N-((S)-2-(2,4-difluorophenyl)-4-oxo-4-(pyrimidin-5-yl)-butan-2-yl)-2-methylpropane-2-sulfinamide

Base Information

• Chemical Name: (R)-N-((S)-2-(2,4-difluorophenyl)-4-oxo-4-(pyrimidin-5-yl)-butan-2-yl)-2-methylpropane-2-sulfinamide
• CAS No.: 1616100-96-9
• Molecular Formula: C₁₈H₂₁F₂N₃O₂S
• Molecular Weight: 381.446
• Mol file: 1616100-96-9.mol

Synonyms:(R)-N-((S)-2-(2,4-difluorophenyl)-4-oxo-4-(pyrimidin-5-yl)-butan-2-yl)-2-methylpropane-2-sulfinamide

Chemical Property of (R)-N-((S)-2-(2,4-difluorophenyl)-4-oxo-4-(pyrimidin-5-yl)-butan-2-yl)-2-methylpropane-2-sulfinamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-N-((S)-2-(2,4-difluorophenyl)-4-oxo-4-(pyrimidin-5-yl)-butan-2-yl)-2-methylpropane-2-sulfinamide

There total 2 articles about (R)-N-((S)-2-(2,4-difluorophenyl)-4-oxo-4-(pyrimidin-5-yl)-butan-2-yl)-2-methylpropane-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: 46.4%

(R,E)-N-(1-(2,4-difluorophenyl)ethylidene)-2-methylpropane-2-sulfinamide (1585971-57-8) + 1-(pyrimidin-5-yl)ethan-1-one (10325-70-9) → (R)-N-((S)-2-(2,4-difluorophenyl)-4-oxo-4-(pyrimidin-5-yl)-butan-2-yl)-2-methylpropane-2-sulfinamide (1616100-96-9)

Guidance literature:

1-(pyrimidin-5-yl)ethan-1-one; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 0.5h; Inert atmosphere;

(R,E)-N-(1-(2,4-difluorophenyl)ethylidene)-2-methylpropane-2-sulfinamide; In N,N-dimethyl-formamide; mineral oil; at -10 - -5 ℃; for 1.5h; Inert atmosphere;

Reference yield:

2',4'-difluoroacetophenone (364-83-0) → (R)-N-((S)-2-(2,4-difluorophenyl)-4-oxo-4-(pyrimidin-5-yl)-butan-2-yl)-2-methylpropane-2-sulfinamide (1616100-96-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: titanium(IV) tetraethanolate / tetrahydrofuran / 16 h / 65 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere

2.2: 1.5 h / -10 - -5 °C / Inert atmosphere

With titanium(IV) tetraethanolate; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil;

Reference yield: 93.0%

(R)-N-((S)-2-(2,4-difluorophenyl)-4-oxo-4-(pyrimidin-5-yl)-butan-2-yl)-2-methylpropane-2-sulfinamide (1616100-96-9) → (R)-N-((2S,4R)-2-(2,4-difluorophenyl)-4-hydroxy-4-(pyrimidin-5-yl)butan-2-yl)-2-methylpropane-2-sulfinamide (1616100-97-0)

Guidance literature:

With lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; diethyl ether; at -78 - -50 ℃; for 1h; stereoselective reaction; Inert atmosphere;

DOI:10.1021/acs.jmedchem.6b01012

upstream raw materials:

(R,E)-N-(1-(2,4-difluorophenyl)ethylidene)-2-methylpropane-2-sulfinamide

1-(pyrimidin-5-yl)ethan-1-one

2',4'-difluoroacetophenone

Downstream raw materials:

(R)-N-((2S,4R)-2-(2,4-difluorophenyl)-4-hydroxy-4-(pyrimidin-5-yl)butan-2-yl)-2-methylpropane-2-sulfinamide

N-(((2S,4R)-2-(2,4-difluorophenyl)-4-hydroxy-4-(pyrimidin-5-yl)butan-2-yl)carbamothioyl)benzamide

(4S,6S)-4-(2,4-difluorophenyl)-4-methyl-6-(pyrimidin-5-yl)-5,6-dihydro-4H-1,3-thiazin-2-amine