(S)-N₁-(2-(2-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-1-yl)phenyl)-N₂-(3,5-dimethylphenyl)oxalamide

Base Information

• Chemical Name: (S)-N₁-(2-(2-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-1-yl)phenyl)-N₂-(3,5-dimethylphenyl)oxalamide
• CAS No.: 1358742-29-6
• Molecular Formula: C₂₇H₃₉N₃O₃Si
• Molecular Weight: 481.71

Synonyms:(S)-N₁-(2-(2-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-1-yl)phenyl)-N₂-(3,5-dimethylphenyl)oxalamide

Chemical Property of (S)-N₁-(2-(2-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-1-yl)phenyl)-N₂-(3,5-dimethylphenyl)oxalamide

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Technology Process of (S)-N₁-(2-(2-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-1-yl)phenyl)-N₂-(3,5-dimethylphenyl)oxalamide

There total 8 articles about (S)-N₁-(2-(2-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-1-yl)phenyl)-N₂-(3,5-dimethylphenyl)oxalamide 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: 46.0%

2-(3,5-dimethylphenylamino)-2-oxoacetic acid (1018295-15-2) + (S)-2-(2-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-1-yl)aniline (1358742-11-6) → (S)-N1-(2-(2-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-1-yl)phenyl)-N2-(3,5-dimethylphenyl)oxalamide (1358742-29-6)

Guidance literature:

2-(3,5-dimethylphenylamino)-2-oxoacetic acid; With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; at 0 ℃; for 1h; Inert atmosphere; Molecular sieve;

(S)-2-(2-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-1-yl)aniline; In tetrahydrofuran; dichloromethane; at 0 - 20 ℃; Inert atmosphere; Molecular sieve;

DOI:10.1016/j.tetasy.2011.11.015

Reference yield:

2-(3,5-dimethylphenylamino)-2-oxoacetic acidethyl ester (333441-77-3) → (S)-N1-(2-(2-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-1-yl)phenyl)-N2-(3,5-dimethylphenyl)oxalamide (1358742-29-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydroxide / tetrahydrofuran; water

1.2: Acidic conditions

2.1: benzotriazol-1-ol; dicyclohexyl-carbodiimide / tetrahydrofuran; dichloromethane / 1 h / 0 °C / Inert atmosphere; Molecular sieve

2.2: 0 - 20 °C / Inert atmosphere; Molecular sieve

With benzotriazol-1-ol; dicyclohexyl-carbodiimide; sodium hydroxide; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/j.tetasy.2011.11.015

Reference yield:

(S)-2-((tert-butyldimethylsilyloxy)methyl)-1-(2-nitrophenyl)pyrrolidine (1358742-08-1) → (S)-N1-(2-(2-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-1-yl)phenyl)-N2-(3,5-dimethylphenyl)oxalamide (1358742-29-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 4 h / 3800.26 Torr

2.1: benzotriazol-1-ol; dicyclohexyl-carbodiimide / tetrahydrofuran; dichloromethane / 1 h / 0 °C / Inert atmosphere; Molecular sieve

2.2: 0 - 20 °C / Inert atmosphere; Molecular sieve

With palladium 10% on activated carbon; hydrogen; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; ethyl acetate;

DOI:10.1016/j.tetasy.2011.11.015

upstream raw materials:

2-(3,5-dimethylphenylamino)-2-oxoacetic acidethyl ester

(S)-2-((tert-butyldimethylsilyloxy)methyl)-1-(2-nitrophenyl)pyrrolidine

2-(3,5-dimethylphenylamino)-2-oxoacetic acid

(S)-2-(2-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-1-yl)aniline

Downstream raw materials:

(S)-(1-(2-(2-(3,5-dimethylphenylamino) ethylamino)phenyl)pyrrolidin-2-yl)methanol

(S)-N₁-(3,5-dimethylphenyl)-N₂-(2-(2-(methoxymethyl)pyrrolidin-1-yl)phenyl)ethane-1,2-diamine

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