(S)-N-(2-(1-(3-ethoxy-4-hydroxyphenyl)-2-(methylsulfonyl)ethyl)-1,3-dioxoisoindolin-4-yl)acetamide

Base Information

• Chemical Name: (S)-N-(2-(1-(3-ethoxy-4-hydroxyphenyl)-2-(methylsulfonyl)ethyl)-1,3-dioxoisoindolin-4-yl)acetamide
• CAS No.: 1384441-38-6
• Molecular Formula: C₂₁H₂₂N₂O₇S
• Molecular Weight: 446.481
• Mol file: 1384441-38-6.mol

Synonyms:(S)-N-(2-(1-(3-ethoxy-4-hydroxyphenyl)-2-(methylsulfonyl)ethyl)-1,3-dioxoisoindolin-4-yl)acetamide

Chemical Property of (S)-N-(2-(1-(3-ethoxy-4-hydroxyphenyl)-2-(methylsulfonyl)ethyl)-1,3-dioxoisoindolin-4-yl)acetamide

Chemical Property:

• Boiling Point: 765.2±60.0 °C(Predicted)
• Density: 1.450±0.06 g/cm3(Predicted)

Purity/Quality:

HPLC ≥ 98% ^*data from raw suppliers

N-[2-[(1S)-1-(3-Ethoxy-4-hydroxyphenyl)-2-(methylsulfonyl)ethyl]-2,3-dihydro-1,3-dioxo-1H-isoindol-4-yl]acetamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: N-[2-[(1S)-1-(3-Ethoxy-4-hydroxyphenyl)-2-(methylsulfonyl)ethyl]-2,3-dihydro-1,3-dioxo-1H-isoindol-4-yl]acetamide is a related compound of Apremilast (A729700), which is?an oral phosphodiesterase 4 inhibitor used for treating psoriatic arthritis. N-[2-[(1S)-1-(3-Ethoxy-4-hydroxyphenyl)-2-(methylsulfonyl)ethyl]-2,3-dihydro-1,3-dioxo-1H-isoindol-4-yl]acetamide may be a useful compound for determining metabolic clearance of apremilast. Apremilast Impurity 7

Technology Process of (S)-N-(2-(1-(3-ethoxy-4-hydroxyphenyl)-2-(methylsulfonyl)ethyl)-1,3-dioxoisoindolin-4-yl)acetamide

There total 1 articles about (S)-N-(2-(1-(3-ethoxy-4-hydroxyphenyl)-2-(methylsulfonyl)ethyl)-1,3-dioxoisoindolin-4-yl)acetamide 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:

Apremilast (608141-41-9) → (S)-N-(2-(1-(3-ethoxy-4-hydroxyphenyl)-2-(methylsulfonyl)ethyl)-1,3-dioxoisoindolin-4-yl)acetamide (1384441-38-6)

Guidance literature:

With trimethylsilyl iodide; In dichloromethane; at 20 ℃; for 24h;

Reference yield: 65.0%

[13C2H3] methyl iodide (20710-47-8,207507-22-0) + (S)-N-(2-(1-(3-ethoxy-4-hydroxyphenyl)-2-(methylsulfonyl)ethyl)-1,3-dioxoisoindolin-4-yl)acetamide (1384441-38-6) → (S)-N-(2-(1-(3-ethoxy-4-([13C, 2H3]methoxy)-phenyl)-2-(methylsulfonyl)ethyl)-1,3-dioxoisoindolin-4-yl)acetamide

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 40 ℃; for 18h;

Reference yield:

(S)-N-(2-(1-(3-ethoxy-4-hydroxyphenyl)-2-(methylsulfonyl)ethyl)-1,3-dioxoisoindolin-4-yl)acetamide (1384441-38-6) → C33H36N2O16S (1384967-22-9)

Guidance literature:

Multi-step reaction with 2 steps

1: boron trifluoride diethyl etherate / dichloromethane / 6 h / -18 - 25 °C / Molecular sieve

2: hydrogen / palladium 10% on activated carbon / ethyl acetate / 12 h / 1551.49 - 2068.65 Torr

With boron trifluoride diethyl etherate; hydrogen; palladium 10% on activated carbon; In dichloromethane; ethyl acetate;

upstream raw materials:

Apremilast

Downstream raw materials:

(S)-N-{2-[1-(3,4-dihydroxy-phenyl)-2-methanesulfonyl-ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}-acetamide

C₃₃H₃₆N₂O₁₆S

(S)-N-{2-[1-(3-ethoxy-4-glucopyranuroxy-phenyl)-2-methanesulfonyl-ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}-acetamide