(3-chloro-4-methylsulfanyl-phenyl)-N-[2(R)-hydroxy-1(R)-methyl-2(R)-phenyl-ethyl]-N-methyl acetamide

Base Information

• Chemical Name: (3-chloro-4-methylsulfanyl-phenyl)-N-[2(R)-hydroxy-1(R)-methyl-2(R)-phenyl-ethyl]-N-methyl acetamide
• CAS No.: 588940-69-6
• Molecular Formula: C₁₉H₂₂ClNO₂S
• Molecular Weight: 363.908
• Mol file: 588940-69-6.mol

Synonyms:(3-chloro-4-methylsulfanyl-phenyl)-N-[2(R)-hydroxy-1(R)-methyl-2(R)-phenyl-ethyl]-N-methyl acetamide

Chemical Property of (3-chloro-4-methylsulfanyl-phenyl)-N-[2(R)-hydroxy-1(R)-methyl-2(R)-phenyl-ethyl]-N-methyl acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3-chloro-4-methylsulfanyl-phenyl)-N-[2(R)-hydroxy-1(R)-methyl-2(R)-phenyl-ethyl]-N-methyl acetamide

There total 5 articles about (3-chloro-4-methylsulfanyl-phenyl)-N-[2(R)-hydroxy-1(R)-methyl-2(R)-phenyl-ethyl]-N-methyl 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: 78.0%

(1R,2R)-pseudoephedrine (321-97-1,7009-81-6,90-83-5,6912-63-6) + (3-chloro-4-methylsulfanyl-phenyl)-acetic acid (87776-75-8) → (3-chloro-4-methylsulfanyl-phenyl)-N-[2(R)-hydroxy-1(R)-methyl-2(R)-phenyl-ethyl]-N-methyl acetamide (588940-69-6)

Guidance literature:

(3-chloro-4-methylsulfanyl-phenyl)-acetic acid; With pivaloyl chloride; potassium carbonate; In acetone; at -10 - 0 ℃; for 1.41667h;

(1R,2R)-pseudoephedrine; In acetone; at -10 - 25 ℃; for 1.16667h;

Reference yield: 78.0%

(1R,2R)-pseudoephedrine (321-97-1,7009-81-6,90-83-5,6912-63-6) + pivaloyl chloride (3282-30-2) + (3-chloro-4-methylsulfanyl-phenyl)-acetic acid (87776-75-8) → (3-chloro-4-methylsulfanyl-phenyl)-N-[2(R)-hydroxy-1(R)-methyl-2(R)-phenyl-ethyl]-N-methyl acetamide (588940-69-6)

Guidance literature:

With potassium carbonate; In acetone;

Reference yield:

(3-chloro-4-methylsulfanyl-phenyl)-oxo-acetic acid methyl ester (393165-02-1) → (3-chloro-4-methylsulfanyl-phenyl)-N-[2(R)-hydroxy-1(R)-methyl-2(R)-phenyl-ethyl]-N-methyl acetamide (588940-69-6)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydroxide; water / toluene / 1.5 h / 50 - 60 °C / Inert atmosphere

2: hydrazine hydrate; potassium hydroxide / 16 h / -50 - 100 °C / Inert atmosphere

3: potassium carbonate; pivaloyl chloride / acetone / 0.33 h / -10 - 20 °C / Inert atmosphere

With water; pivaloyl chloride; potassium carbonate; hydrazine hydrate; potassium hydroxide; sodium hydroxide; In acetone; toluene;

DOI:10.1021/jm3008689

upstream raw materials:

(1R,2R)-pseudoephedrine

pivaloyl chloride

(3-chloro-4-methylsulfanyl-phenyl)-acetic acid

2-chlorothioanisole

Downstream raw materials:

(2R)-2-[3-chloro-4-(methylsulfanyl)phenyl]-3-cyclopentyl-N-[(1R,2R)-1-hydroxy-1-phenylpropan-2-yl]-N-methylpropanamide

RO 0505082

(R)-2-(3-chloro-4-(methylsulfonyl)phenyl)-3-cyclopentylpropanoic acid

(2R)-2-[3-chloro-4-(methylsulfanyl)phenyl]-3-cyclopentylpropanoic acid