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

Base Information

• Chemical Name: (S)-N-{2-[1-(3-ethoxy-4-glucopyranuroxy-phenyl)-2-methanesulfonyl-ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}-acetamide
• CAS No.: 1384814-89-4
• Molecular Formula: C₂₇H₃₀N₂O₁₃S
• Molecular Weight: 622.607
• Mol file: 1384814-89-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about (S)-N-{2-[1-(3-ethoxy-4-glucopyranuroxy-phenyl)-2-methanesulfonyl-ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-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:

C33H36N2O16S (1384967-22-9) → (S)-N-{2-[1-(3-ethoxy-4-glucopyranuroxy-phenyl)-2-methanesulfonyl-ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}-acetamide (1384814-89-4)

Guidance literature:

With sodium carbonate; In methanol; at 60 ℃; for 2h;

Reference yield:

(2S,3R,4S,5S,6S)-2-(4-((S)-1-(4-acetamido-1,3-dioxoisoindolin-2-yl)-2-(methylsulfonyl)ethyl)-2-ethoxyphenoxy)-6-((benzyloxy)carbonyl)tetrahydro-2H-pyran-3,4,5-triyltriacetate (1384967-21-8) → (S)-N-{2-[1-(3-ethoxy-4-glucopyranuroxy-phenyl)-2-methanesulfonyl-ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}-acetamide (1384814-89-4)

Guidance literature:

Multi-step reaction with 2 steps

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

2: sodium carbonate / methanol / 2 h / 60 °C

With hydrogen; sodium carbonate; palladium 10% on activated carbon; In methanol; ethyl acetate;

Reference yield:

Apremilast (608141-41-9) → (S)-N-{2-[1-(3-ethoxy-4-glucopyranuroxy-phenyl)-2-methanesulfonyl-ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}-acetamide (1384814-89-4)

Guidance literature:

Multi-step reaction with 4 steps

1: trimethylsilyl iodide / dichloromethane / 24 h / 20 °C

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

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

4: sodium carbonate / methanol / 2 h / 60 °C

With trimethylsilyl iodide; boron trifluoride diethyl etherate; hydrogen; sodium carbonate; palladium 10% on activated carbon; In methanol; dichloromethane; ethyl acetate;

upstream raw materials:

Apremilast

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

(2S,3R,4S,5S,6S)-2-(4-((S)-1-(4-acetamido-1,3-dioxoisoindolin-2-yl)-2-(methylsulfonyl)ethyl)-2-ethoxyphenoxy)-6-((benzyloxy)carbonyl)tetrahydro-2H-pyran-3,4,5-triyltriacetate

C₃₃H₃₆N₂O₁₆S