3-{4-[9-(3-hydroxy-butoxy)-3,6-dimethoxy-10-oxo-9,10-dihydro-10λ⁴-thioxanthen-9-yl]-phenyl}-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester

Base Information

• Chemical Name: 3-{4-[9-(3-hydroxy-butoxy)-3,6-dimethoxy-10-oxo-9,10-dihydro-10λ⁴-thioxanthen-9-yl]-phenyl}-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester
• CAS No.: 880570-33-2
• Molecular Formula: C₃₂H₃₃NO₉S
• Molecular Weight: 607.681

Synonyms:3-{4-[9-(3-hydroxy-butoxy)-3,6-dimethoxy-10-oxo-9,10-dihydro-10λ⁴-thioxanthen-9-yl]-phenyl}-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester

Chemical Property of 3-{4-[9-(3-hydroxy-butoxy)-3,6-dimethoxy-10-oxo-9,10-dihydro-10λ⁴-thioxanthen-9-yl]-phenyl}-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester

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Technology Process of 3-{4-[9-(3-hydroxy-butoxy)-3,6-dimethoxy-10-oxo-9,10-dihydro-10λ⁴-thioxanthen-9-yl]-phenyl}-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester

There total 6 articles about 3-{4-[9-(3-hydroxy-butoxy)-3,6-dimethoxy-10-oxo-9,10-dihydro-10λ⁴-thioxanthen-9-yl]-phenyl}-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester 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:

3,6-dimethoxy-9H-thioxanthen-9-one → 3-{4-[9-(3-hydroxy-butoxy)-3,6-dimethoxy-10-oxo-9,10-dihydro-10λ4-thioxanthen-9-yl]-phenyl}-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester (880570-33-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: t-BuLi / pentane; tetrahydrofuran / 1 h / -80 - -40 °C

1.2: 56 percent / pentane; tetrahydrofuran / -80 - 20 °C

2.1: aq. trifluoroacetic acid / tetrahydrofuran / 1 h

2.2: LiOH / aq. ethanol / 20 °C

3.1: Et₃N / acetonitrile; dimethylformamide / 2 h / 20 °C

4.1: HBF₄ / acetonitrile; diethyl ether / 0.17 h

4.2: DIEA / acetonitrile / 0.5 h / 20 °C

5.1: MCPBA

With tetrafluoroboric acid; tert.-butyl lithium; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; acetonitrile; pentane;

DOI:10.1039/b504913j

Reference yield:

1-[2-(4-bromophenyl)ethyl]-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane (845272-39-1) → 3-{4-[9-(3-hydroxy-butoxy)-3,6-dimethoxy-10-oxo-9,10-dihydro-10λ4-thioxanthen-9-yl]-phenyl}-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester (880570-33-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: t-BuLi / pentane; tetrahydrofuran / 1 h / -80 - -40 °C

1.2: 56 percent / pentane; tetrahydrofuran / -80 - 20 °C

2.1: aq. trifluoroacetic acid / tetrahydrofuran / 1 h

2.2: LiOH / aq. ethanol / 20 °C

3.1: Et₃N / acetonitrile; dimethylformamide / 2 h / 20 °C

4.1: HBF₄ / acetonitrile; diethyl ether / 0.17 h

4.2: DIEA / acetonitrile / 0.5 h / 20 °C

5.1: MCPBA

With tetrafluoroboric acid; tert.-butyl lithium; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; acetonitrile; pentane;

DOI:10.1039/b504913j

Reference yield:

3-[4-(9-hydroxy-3,6-dimethoxy-9H-thioxanthen-9-yl)-phenyl]-propionic acid → 3-{4-[9-(3-hydroxy-butoxy)-3,6-dimethoxy-10-oxo-9,10-dihydro-10λ4-thioxanthen-9-yl]-phenyl}-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester (880570-33-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Et₃N / acetonitrile; dimethylformamide / 2 h / 20 °C

2.1: HBF₄ / acetonitrile; diethyl ether / 0.17 h

2.2: DIEA / acetonitrile / 0.5 h / 20 °C

3.1: MCPBA

With tetrafluoroboric acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; In diethyl ether; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1039/b504913j

upstream raw materials:

1-[2-(4-bromophenyl)ethyl]-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane

1-{2-[4-(9-hydroxy-3,6-dimethoxythioxanthen-9-yl)phenyl]ethyl}-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane

3-[4-(9-hydroxy-3,6-dimethoxythioxanthen-9-yl)phenyl]propionic acid N-oxysuccinimide ester

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