methyl (S)-2-((4,5-dimethoxy-2-nitrobenzyloxy)carbonyl)-3-(1-tosyl-1H-pyrrolo[3,2-c]isoquinolin-3-yl)propanoate

Base Information

• Chemical Name: methyl (S)-2-((4,5-dimethoxy-2-nitrobenzyloxy)carbonyl)-3-(1-tosyl-1H-pyrrolo[3,2-c]isoquinolin-3-yl)propanoate
• CAS No.: 1533429-81-0
• Molecular Formula: C₃₂H₃₀N₄O₁₀S
• Molecular Weight: 662.677

Synonyms:methyl (S)-2-((4,5-dimethoxy-2-nitrobenzyloxy)carbonyl)-3-(1-tosyl-1H-pyrrolo[3,2-c]isoquinolin-3-yl)propanoate

Chemical Property of methyl (S)-2-((4,5-dimethoxy-2-nitrobenzyloxy)carbonyl)-3-(1-tosyl-1H-pyrrolo[3,2-c]isoquinolin-3-yl)propanoate

Chemical Property:

Purity/Quality:

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Technology Process of methyl (S)-2-((4,5-dimethoxy-2-nitrobenzyloxy)carbonyl)-3-(1-tosyl-1H-pyrrolo[3,2-c]isoquinolin-3-yl)propanoate

There total 11 articles about methyl (S)-2-((4,5-dimethoxy-2-nitrobenzyloxy)carbonyl)-3-(1-tosyl-1H-pyrrolo[3,2-c]isoquinolin-3-yl)propanoate 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: 90.0%

nitroveratryloxycarbonyl chloride (42855-00-5) + methyl (S)-2-Amino-3-(1-tosyl-1H-pyrrolo[3,2-c]isoquinolin-3-yl)propanoate (1533429-80-9) → methyl (S)-2-((4,5-dimethoxy-2-nitrobenzyloxy)carbonyl)-3-(1-tosyl-1H-pyrrolo[3,2-c]isoquinolin-3-yl)propanoate (1533429-81-0)

Guidance literature:

With potassium carbonate; In 1,4-dioxane; water; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1021/ol403429e

Reference yield:

4-amino-3-acetylenetrimethylsililisoquinoline (271784-16-8) → methyl (S)-2-((4,5-dimethoxy-2-nitrobenzyloxy)carbonyl)-3-(1-tosyl-1H-pyrrolo[3,2-c]isoquinolin-3-yl)propanoate (1533429-81-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sodium amide / N,N-dimethyl-formamide / 16 h / 100 °C / Inert atmosphere

2.1: hexamethylenetetramine / water / Inert atmosphere; Reflux

3.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 0 °C / Inert atmosphere

3.2: 3 h / 0 °C / Inert atmosphere

4.1: sodium tetrahydroborate / ethanol / 2 h / 20 °C

5.1: triethylamine; thionyl chloride / dichloromethane / -10 - 20 °C / Inert atmosphere

6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

6.2: -78 - 20 °C / Inert atmosphere

7.1: hydrogenchloride / tetrahydrofuran; water / 2 h / 0 - 20 °C

8.1: potassium carbonate / water; 1,4-dioxane / 12 h / 20 °C / Inert atmosphere

With hydrogenchloride; sodium tetrahydroborate; n-butyllithium; thionyl chloride; hexamethylenetetramine; sodium hydride; potassium carbonate; sodium amide; triethylamine; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/ol403429e

Reference yield:

4-bromoisoquinoline (1532-97-4) → methyl (S)-2-((4,5-dimethoxy-2-nitrobenzyloxy)carbonyl)-3-(1-tosyl-1H-pyrrolo[3,2-c]isoquinolin-3-yl)propanoate (1533429-81-0)

Guidance literature:

Multi-step reaction with 11 steps

1.1: copper; copper(l) chloride; ammonium hydroxide / 16 h / 100 °C / Sealed tube

2.1: iodine; silver sulfate / ethanol / 16 h / 23 °C / Darkness

3.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine; copper(l) iodide / tetrahydrofuran / 16 h / 23 °C / Inert atmosphere

4.1: sodium amide / N,N-dimethyl-formamide / 16 h / 100 °C / Inert atmosphere

5.1: hexamethylenetetramine / water / Inert atmosphere; Reflux

6.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 0 °C / Inert atmosphere

6.2: 3 h / 0 °C / Inert atmosphere

7.1: sodium tetrahydroborate / ethanol / 2 h / 20 °C

8.1: triethylamine; thionyl chloride / dichloromethane / -10 - 20 °C / Inert atmosphere

9.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

9.2: -78 - 20 °C / Inert atmosphere

10.1: hydrogenchloride / tetrahydrofuran; water / 2 h / 0 - 20 °C

11.1: potassium carbonate / water; 1,4-dioxane / 12 h / 20 °C / Inert atmosphere

With hydrogenchloride; bis-triphenylphosphine-palladium(II) chloride; ammonium hydroxide; sodium tetrahydroborate; copper(l) iodide; n-butyllithium; thionyl chloride; hexamethylenetetramine; iodine; copper; sodium hydride; potassium carbonate; silver sulfate; sodium amide; triethylamine; copper(l) chloride; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/ol403429e

upstream raw materials:

4-amino-3-acetylenetrimethylsililisoquinoline

1H-pyrrolo[3,2-c]isoquinoline

1H-pyrrolo[3,2-c]isoquinoline-3-carbaldehyde

4-bromoisoquinoline

Downstream raw materials:

methyl (S)-2-((4,5-dimethoxy-2-nitrobenzyloxy)carbonyl)-3-(1H-pyrrolo[3,2-c]isoquinolin-3-yl)propanoate

cyanomethyl (S)-2-((4,5-dimethoxy-2-nitrobenzyloxy)carbonyl)-3-(1H-pyrrolo[3,2-c]isoquinolin-3-yl)propanoate

(S)-2-((4,5-dimethoxy-2-nitrobenzyloxy)carbonyl)-3-(1H-pyrrolo[3,2-c]isoquinolin-3-yl)-pdCpA

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