N₁-((5S,5aS,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydro[1,3]dioxolo[4',5':4,5]benzo[f]isobenzofuran-5-yl)-4-((((2-chloroethyl)amino)carbonyl)amino)benzamide

Base Information

• Chemical Name: N₁-((5S,5aS,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydro[1,3]dioxolo[4',5':4,5]benzo[f]isobenzofuran-5-yl)-4-((((2-chloroethyl)amino)carbonyl)amino)benzamide
• CAS No.: 1449741-71-2
• Molecular Formula: C₃₂H₃₂ClN₃O₉
• Molecular Weight: 638.074

Synonyms:N₁-((5S,5aS,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydro[1,3]dioxolo[4',5':4,5]benzo[f]isobenzofuran-5-yl)-4-((((2-chloroethyl)amino)carbonyl)amino)benzamide

Chemical Property of N₁-((5S,5aS,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydro[1,3]dioxolo[4',5':4,5]benzo[f]isobenzofuran-5-yl)-4-((((2-chloroethyl)amino)carbonyl)amino)benzamide

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Technology Process of N₁-((5S,5aS,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydro[1,3]dioxolo[4',5':4,5]benzo[f]isobenzofuran-5-yl)-4-((((2-chloroethyl)amino)carbonyl)amino)benzamide

There total 4 articles about N₁-((5S,5aS,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydro[1,3]dioxolo[4',5':4,5]benzo[f]isobenzofuran-5-yl)-4-((((2-chloroethyl)amino)carbonyl)amino)benzamide 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: 66.0%

2-chloroethyl isothiocyanate (1943-83-5) + N1-((5S,5aS,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydro[1,3]dioxolo[4',5':4,5]benzo[f]isobenzofuran-5-yl)-4-aminobenzamide (1365699-34-8) → N1-((5S,5aS,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydro[1,3]dioxolo[4',5':4,5]benzo[f]isobenzofuran-5-yl)-4-((((2-chloroethyl)amino)carbonyl)amino)benzamide (1449741-71-2)

Guidance literature:

In dichloromethane; at 0 - 20 ℃; for 1h;

DOI:10.1016/j.bmc.2013.06.033

Reference yield:

N1-((5S,5aS,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydro[1,3]dioxolo[4',5':4,5]benzo[f]isobenzofuran-5-yl)-4-nitrobenzamide (1365699-32-6) → N1-((5S,5aS,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydro[1,3]dioxolo[4',5':4,5]benzo[f]isobenzofuran-5-yl)-4-((((2-chloroethyl)amino)carbonyl)amino)benzamide (1449741-71-2)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen; palladium 10% on activated carbon / ethyl acetate / 12 h / 20 °C

2: dichloromethane / 1 h / 0 - 20 °C

With palladium 10% on activated carbon; hydrogen; In dichloromethane; ethyl acetate;

DOI:10.1016/j.bmc.2013.06.033

Reference yield:

4β-amino-4-deoxypodophyllotoxin (155252-35-0) → N1-((5S,5aS,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydro[1,3]dioxolo[4',5':4,5]benzo[f]isobenzofuran-5-yl)-4-((((2-chloroethyl)amino)carbonyl)amino)benzamide (1449741-71-2)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere

2: hydrogen; palladium 10% on activated carbon / ethyl acetate / 12 h / 20 °C

3: dichloromethane / 1 h / 0 - 20 °C

With palladium 10% on activated carbon; hydrogen; triethylamine; In dichloromethane; ethyl acetate;

DOI:10.1016/j.bmc.2013.06.033

upstream raw materials:

2-chloroethyl isothiocyanate

N₁-((5S,5aS,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydro[1,3]dioxolo[4',5':4,5]benzo[f]isobenzofuran-5-yl)-4-aminobenzamide

4β-amino-4-deoxypodophyllotoxin

4-nitro-benzoyl chloride

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