(R)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethanamine (R)-2-acetamido-4-methylpentanoate

Base Information

• Chemical Name: (R)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethanamine (R)-2-acetamido-4-methylpentanoate
• CAS No.: 608142-28-5
• Molecular Formula: C₈H₁₅NO₃*C₁₂H₁₉NO₄S
• Molecular Weight: 446.565
• Mol file: 608142-28-5.mol

Synonyms:(R)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethylamine N-acetyl-D-leucine salt

Chemical Property of (R)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethanamine (R)-2-acetamido-4-methylpentanoate

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (R)-1-(3-Ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethylamine N-Acetyl-D-leucine Salt is an intermediate in the synthesis of (R)-Apremilast (A729705), an enantiomer of Apremilast (A729700), an oral phosphodiesterase 4 inhibitor is used in the treatment of psoriatic arthritis.

Technology Process of (R)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethanamine (R)-2-acetamido-4-methylpentanoate

There total 4 articles about (R)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethanamine (R)-2-acetamido-4-methylpentanoate 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:

2-(3-ethoxy-4-methoxyphenyl)-1-(methylsulfonyl)eth-2-ylamine (253168-94-4) + N-acetyl-D-leucine (19764-30-8) → (R)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethylamine N-acetyl-D-leucine salt (608142-28-5)

Guidance literature:

In methanol; at 20 ℃; for 8h; Reflux; Inert atmosphere;

Reference yield:

isovanillin (621-59-0) → (R)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethylamine N-acetyl-D-leucine salt (608142-28-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C / Inert atmosphere

2.2: 20 °C / Cooling with salt-ice; Inert atmosphere

3.1: hydrogenchloride; water / diethyl ether / 0.5 h / 20 °C

3.2: pH 12 / Cooling with ice

4.1: methanol / 8 h / 20 °C / Reflux; Inert atmosphere

With hydrogenchloride; n-butyllithium; water; potassium carbonate; In tetrahydrofuran; methanol; diethyl ether; hexane; N,N-dimethyl-formamide;

Reference yield:

3-ethoxy-4-methoxybenzaldehyde (1131-52-8) → (R)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethylamine N-acetyl-D-leucine salt (608142-28-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C / Inert atmosphere

1.2: 20 °C / Cooling with salt-ice; Inert atmosphere

2.1: hydrogenchloride; water / diethyl ether / 0.5 h / 20 °C

2.2: pH 12 / Cooling with ice

3.1: methanol / 8 h / 20 °C / Reflux; Inert atmosphere

With hydrogenchloride; n-butyllithium; water; In tetrahydrofuran; methanol; diethyl ether; hexane;

upstream raw materials:

isovanillin

3-ethoxy-4-methoxybenzaldehyde

1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)-N-(trimethylsilyl)ethylamine

2-(3-ethoxy-4-methoxyphenyl)-1-(methylsulfonyl)eth-2-ylamine

Downstream raw materials:

(R)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)-ethylamine

Refernces