rac-4-(((2S,3S,4S)-2-(3-chloro-2-fluorophenyl)-3-(4-chloro-2-fluorophenyl)-3-cyano-4-neopentylpyrrolidine-1-carboxamido)methyl)-2-methoxybenzoic acid

Base Information

• Chemical Name: rac-4-(((2S,3S,4S)-2-(3-chloro-2-fluorophenyl)-3-(4-chloro-2-fluorophenyl)-3-cyano-4-neopentylpyrrolidine-1-carboxamido)methyl)-2-methoxybenzoic acid
• CAS No.: 1289570-73-5
• Molecular Formula: C₃₂H₃₁Cl₂F₂N₃O₄
• Molecular Weight: 630.519
• Mol file: 1289570-73-5.mol

Synonyms:

Chemical Property of rac-4-(((2S,3S,4S)-2-(3-chloro-2-fluorophenyl)-3-(4-chloro-2-fluorophenyl)-3-cyano-4-neopentylpyrrolidine-1-carboxamido)methyl)-2-methoxybenzoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of rac-4-(((2S,3S,4S)-2-(3-chloro-2-fluorophenyl)-3-(4-chloro-2-fluorophenyl)-3-cyano-4-neopentylpyrrolidine-1-carboxamido)methyl)-2-methoxybenzoic acid

There total 10 articles about rac-4-(((2S,3S,4S)-2-(3-chloro-2-fluorophenyl)-3-(4-chloro-2-fluorophenyl)-3-cyano-4-neopentylpyrrolidine-1-carboxamido)methyl)-2-methoxybenzoic acid 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:

rac-4-(((2S,3S,4S)-2-(3-chloro-2-fluorophenyl)-3-(4-chloro-2-fluorophenyl)-3-cyano-4-neopentylpyrrolidine-1-carboxamido)methyl)-2-methoxybenzoic acid → rac-4-(((2S,3S,4S)-2-(3-chloro-2-fluorophenyl)-3-(4-chloro-2-fluorophenyl)-3-cyano-4-neopentylpyrrolidine-1-carboxamido)methyl)-2-methoxybenzoic acid (1289570-73-5) + 4-(((2R,3R,4R)-2-(3-chloro-2-fluorophenyl)-3-(4-chloro-2-fluorophenyl)-3-cyano-4-neopentylpyrrolidine-1-carboxamido)methyl)-2-methoxybenzoic acid (1289570-74-6)

Guidance literature:

With Kromasil 5-CelluCoat OD prep column; In methanol; Purification / work up; Resolution of racemate;

Reference yield:

2-methoxy-4-cyano-benzoic acid (89469-52-3) → rac-4-(((2S,3S,4S)-2-(3-chloro-2-fluorophenyl)-3-(4-chloro-2-fluorophenyl)-3-cyano-4-neopentylpyrrolidine-1-carboxamido)methyl)-2-methoxybenzoic acid (1289570-73-5) + 4-(((2R,3R,4R)-2-(3-chloro-2-fluorophenyl)-3-(4-chloro-2-fluorophenyl)-3-cyano-4-neopentylpyrrolidine-1-carboxamido)methyl)-2-methoxybenzoic acid (1289570-74-6)

Guidance literature:

Multi-step reaction with 6 steps

1: toluene-4-sulfonic acid / water / 16 h / Reflux; Inert atmosphere

2: hydrogen / Raney-nickel / water; methanol / 16 h / 2585.81 Torr

3: N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere

4: dichloromethane / 16 h / 20 °C

5: water; lithium hydroxide / tetrahydrofuran / 48 h / 20 °C

6: Kromasil 5-CelluCoat OD prep column / methanol / Resolution of racemate

With water; hydrogen; toluene-4-sulfonic acid; lithium hydroxide; Raney-nickel; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

Reference yield:

2-fluoro-3-chlorobenzaldehyde (85070-48-0) → rac-4-(((2S,3S,4S)-2-(3-chloro-2-fluorophenyl)-3-(4-chloro-2-fluorophenyl)-3-cyano-4-neopentylpyrrolidine-1-carboxamido)methyl)-2-methoxybenzoic acid (1289570-73-5) + 4-(((2R,3R,4R)-2-(3-chloro-2-fluorophenyl)-3-(4-chloro-2-fluorophenyl)-3-cyano-4-neopentylpyrrolidine-1-carboxamido)methyl)-2-methoxybenzoic acid (1289570-74-6)

Guidance literature:

Multi-step reaction with 5 steps

1: dichloromethane; tetrahydrofuran / 20 °C

2: potassium hydroxide / dimethyl sulfoxide / 20 °C

3: dichloromethane / 16 h / 20 °C

4: water; lithium hydroxide / tetrahydrofuran / 48 h / 20 °C

5: Kromasil 5-CelluCoat OD prep column / methanol / Resolution of racemate

With water; lithium hydroxide; potassium hydroxide; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide;

upstream raw materials:

2-(4-chloro-2-fluoro-phenyl)acetonitrile

methyl 4-(aminomethyl)-2-methoxybenzoate

4-{[(imidazole-1-carbonyl)-amino]-methyl}-2-methoxy-benzoic acid methyl ester

[1-(3-chloro-2-fluorophenyl)meth-(E)-ylidene]methylamine