N₁-[(3S)-1-(2-cyano-4-nitrophenyl)-3-pyrrolidinyl]-N₂-{[(1,1-dimethylethyl)oxy]carbonyl}-L-norleucinamide

Base Information

• Chemical Name: N₁-[(3S)-1-(2-cyano-4-nitrophenyl)-3-pyrrolidinyl]-N₂-{[(1,1-dimethylethyl)oxy]carbonyl}-L-norleucinamide
• CAS No.: 1269407-22-8
• Molecular Formula: C₂₂H₃₁N₅O₅
• Molecular Weight: 445.519

Synonyms:N₁-[(3S)-1-(2-cyano-4-nitrophenyl)-3-pyrrolidinyl]-N₂-{[(1,1-dimethylethyl)oxy]carbonyl}-L-norleucinamide

Chemical Property of N₁-[(3S)-1-(2-cyano-4-nitrophenyl)-3-pyrrolidinyl]-N₂-{[(1,1-dimethylethyl)oxy]carbonyl}-L-norleucinamide

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Technology Process of N₁-[(3S)-1-(2-cyano-4-nitrophenyl)-3-pyrrolidinyl]-N₂-{[(1,1-dimethylethyl)oxy]carbonyl}-L-norleucinamide

There total 3 articles about N₁-[(3S)-1-(2-cyano-4-nitrophenyl)-3-pyrrolidinyl]-N₂-{[(1,1-dimethylethyl)oxy]carbonyl}-L-norleucinamide 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: 91.0%

2-[(3S)-3-amino-1-pyrrolidinyl]-5-nitrobenzonitrile hydrochloride (1269406-70-3) + Boc-Nle-OH (6404-28-0) → N1-[(3S)-1-(2-cyano-4-nitrophenyl)-3-pyrrolidinyl]-N2-{[(1,1-dimethylethyl)oxy]carbonyl}-L-norleucinamide (1269407-22-8)

Guidance literature:

With triethylamine; HATU; In dichloromethane; at 20 ℃; for 2h;

Reference yield:

2-fluoro-5-nitrobenzonitrile (17417-09-3) → N1-[(3S)-1-(2-cyano-4-nitrophenyl)-3-pyrrolidinyl]-N2-{[(1,1-dimethylethyl)oxy]carbonyl}-L-norleucinamide (1269407-22-8)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate / acetonitrile / 1 h / 20 °C

2: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C

3: triethylamine; HATU / dichloromethane / 2 h / 20 °C

With hydrogenchloride; potassium carbonate; triethylamine; HATU; In 1,4-dioxane; dichloromethane; acetonitrile;

Reference yield:

1,1-dimethylethyl [(3S)-1-(2-cyano-4-nitrophenyl)-3-pyrrolidinyl]carbamate (1269406-69-0) → N1-[(3S)-1-(2-cyano-4-nitrophenyl)-3-pyrrolidinyl]-N2-{[(1,1-dimethylethyl)oxy]carbonyl}-L-norleucinamide (1269407-22-8)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C

2: triethylamine; HATU / dichloromethane / 2 h / 20 °C

With hydrogenchloride; triethylamine; HATU; In 1,4-dioxane; dichloromethane;

upstream raw materials:

2-[(3S)-3-amino-1-pyrrolidinyl]-5-nitrobenzonitrile hydrochloride

Boc-Nle-OH

2-fluoro-5-nitrobenzonitrile

1,1-dimethylethyl [(3S)-1-(2-cyano-4-nitrophenyl)-3-pyrrolidinyl]carbamate

Downstream raw materials:

N₁-[(3S)-1-(2-cyano-4-nitrophenyl)-3-pyrrolidinyl]-L-norleucinamide hydrochloride

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