(S)-N₁-(2-(2-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-1-yl)phenyl)-N₂-mesityloxalamide

Base Information

• Chemical Name: (S)-N₁-(2-(2-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-1-yl)phenyl)-N₂-mesityloxalamide
• CAS No.: 1358742-35-4
• Molecular Formula: C₂₈H₄₁N₃O₃Si
• Molecular Weight: 495.737

Synonyms:(S)-N₁-(2-(2-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-1-yl)phenyl)-N₂-mesityloxalamide

Chemical Property of (S)-N₁-(2-(2-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-1-yl)phenyl)-N₂-mesityloxalamide

Chemical Property:

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Technology Process of (S)-N₁-(2-(2-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-1-yl)phenyl)-N₂-mesityloxalamide

There total 8 articles about (S)-N₁-(2-(2-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-1-yl)phenyl)-N₂-mesityloxalamide 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: 72.0%

2-(2,4,6-trimethylphenylamino)-2-oxoacetic acid (79354-46-4) + (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-mesityloxalamide (1358742-35-4)

Guidance literature:

2-(2,4,6-trimethylphenylamino)-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:

(S)-2-((tert-butyldimethylsilyloxy)methyl)-1-(2-nitrophenyl)pyrrolidine (1358742-08-1) → (S)-N1-(2-(2-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-1-yl)phenyl)-N2-mesityloxalamide (1358742-35-4)

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

Reference yield:

2-(2,4,6-trimethylphenylamino)-2-oxoacetic acid ethyl ester (79354-30-6) → (S)-N1-(2-(2-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-1-yl)phenyl)-N2-mesityloxalamide (1358742-35-4)

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

upstream raw materials:

2-(2,4,6-trimethylphenylamino)-2-oxoacetic acid

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

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

2-(2,4,6-trimethylphenylamino)-2-oxoacetic acid ethyl ester

Downstream raw materials:

(S)-(1-(2-(2-(mesitylamino)ethylamino)phenyl)pyrrolidin-2-yl)methanol

(S)-N₁-(2-(2-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-1-yl)phenyl)-N₂-mesitylethane-1,2-diamine

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