benzyl (S)-N-(1-(2-(3-(1,3-dioxolan-2-yl)pyridin-2-yl)pyridin-3-ylcarbamoyl)-2-phenylethyl)carbamate

Base Information

• Chemical Name: benzyl (S)-N-(1-(2-(3-(1,3-dioxolan-2-yl)pyridin-2-yl)pyridin-3-ylcarbamoyl)-2-phenylethyl)carbamate
• CAS No.: 1449430-15-2
• Molecular Formula: C₃₀H₂₈N₄O₅
• Molecular Weight: 524.576

Synonyms:benzyl (S)-N-(1-(2-(3-(1,3-dioxolan-2-yl)pyridin-2-yl)pyridin-3-ylcarbamoyl)-2-phenylethyl)carbamate

Chemical Property of benzyl (S)-N-(1-(2-(3-(1,3-dioxolan-2-yl)pyridin-2-yl)pyridin-3-ylcarbamoyl)-2-phenylethyl)carbamate

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Technology Process of benzyl (S)-N-(1-(2-(3-(1,3-dioxolan-2-yl)pyridin-2-yl)pyridin-3-ylcarbamoyl)-2-phenylethyl)carbamate

There total 5 articles about benzyl (S)-N-(1-(2-(3-(1,3-dioxolan-2-yl)pyridin-2-yl)pyridin-3-ylcarbamoyl)-2-phenylethyl)carbamate 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: 65.0%

N-Cbz-L-Phe (1161-13-3) + 2-(3-(1,3-dioxolan-2-yl)pyridin-2-yl)pyridin-3-amine (1449430-11-8) → benzyl (S)-N-(1-(2-(3-(1,3-dioxolan-2-yl)pyridin-2-yl)pyridin-3-ylcarbamoyl)-2-phenylethyl)carbamate (1449430-15-2)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1002/cjoc.201300090

Reference yield:

2-bromopyridine-3-carboxaldehyde (128071-75-0) → benzyl (S)-N-(1-(2-(3-(1,3-dioxolan-2-yl)pyridin-2-yl)pyridin-3-ylcarbamoyl)-2-phenylethyl)carbamate (1449430-15-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: toluene-4-sulfonic acid / benzene / 2.5 h / 80 °C / Inert atmosphere; Molecular sieve

2.1: n-butyllithium / diethyl ether; hexane / 0.5 h / -78 °C / Inert atmosphere

2.2: 3 h / -78 °C / Inert atmosphere

3.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(I) bromide / tetrahydrofuran / 4.5 h / 67 °C / Inert atmosphere

4.1: hydrogen; platinum(IV) oxide trihydrate / ethanol / 20 °C / 760.05 Torr

5.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; platinum(IV) oxide trihydrate; hydrogen; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; copper(I) bromide; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; benzene; 3.1: |Stille Cross Coupling;

DOI:10.1002/cjoc.201300090

Reference yield:

2-bromo-3-(1,3-dioxolan-2-yl)pyridine (153836-97-6) → benzyl (S)-N-(1-(2-(3-(1,3-dioxolan-2-yl)pyridin-2-yl)pyridin-3-ylcarbamoyl)-2-phenylethyl)carbamate (1449430-15-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-butyllithium / diethyl ether; hexane / 0.5 h / -78 °C / Inert atmosphere

1.2: 3 h / -78 °C / Inert atmosphere

2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(I) bromide / tetrahydrofuran / 4.5 h / 67 °C / Inert atmosphere

3.1: hydrogen; platinum(IV) oxide trihydrate / ethanol / 20 °C / 760.05 Torr

4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; platinum(IV) oxide trihydrate; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; copper(I) bromide; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; 2.1: |Stille Cross Coupling;

DOI:10.1002/cjoc.201300090

upstream raw materials:

N-Cbz-L-Phe

2-(3-(1,3-dioxolan-2-yl)pyridin-2-yl)pyridin-3-amine

2-bromopyridine-3-carboxaldehyde

2-bromo-3-(1,3-dioxolan-2-yl)pyridine

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