3-((2S,5R)-4-oxo-5-(2-oxo-2-((2-(3-ethoxy-4-methoxyphenyl)(²H₄)ethyl)amino)ethyl)-2-(4-((phenyl)ethynyl)phenyl)thiazolidin-3-yl)benzamide

Base Information

• Chemical Name: 3-((2S,5R)-4-oxo-5-(2-oxo-2-((2-(3-ethoxy-4-methoxyphenyl)(²H₄)ethyl)amino)ethyl)-2-(4-((phenyl)ethynyl)phenyl)thiazolidin-3-yl)benzamide
• CAS No.: 1449715-37-0
• Molecular Formula: C₃₇H₃₅N₃O₅S
• Molecular Weight: 637.736

Synonyms:3-((2S,5R)-4-oxo-5-(2-oxo-2-((2-(3-ethoxy-4-methoxyphenyl)(²H₄)ethyl)amino)ethyl)-2-(4-((phenyl)ethynyl)phenyl)thiazolidin-3-yl)benzamide

Chemical Property of 3-((2S,5R)-4-oxo-5-(2-oxo-2-((2-(3-ethoxy-4-methoxyphenyl)(²H₄)ethyl)amino)ethyl)-2-(4-((phenyl)ethynyl)phenyl)thiazolidin-3-yl)benzamide

Chemical Property:

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Technology Process of 3-((2S,5R)-4-oxo-5-(2-oxo-2-((2-(3-ethoxy-4-methoxyphenyl)(²H₄)ethyl)amino)ethyl)-2-(4-((phenyl)ethynyl)phenyl)thiazolidin-3-yl)benzamide

There total 6 articles about 3-((2S,5R)-4-oxo-5-(2-oxo-2-((2-(3-ethoxy-4-methoxyphenyl)(²H₄)ethyl)amino)ethyl)-2-(4-((phenyl)ethynyl)phenyl)thiazolidin-3-yl)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: 68.0%

3-[(2S,5R)-5-aminomethyl-4-oxo-2-(4-phenylethynyl-phenyl)-thiazolidin-3-yl]-benzamide (1449715-46-1) + 3-(3-ethoxy-4-methoxyphenyl)(2H4)propanoic acid (1398065-51-4) → 3-((2S,5R)-4-oxo-5-(2-oxo-2-((2-(3-ethoxy-4-methoxyphenyl)(2H4)ethyl)amino)ethyl)-2-(4-((phenyl)ethynyl)phenyl)thiazolidin-3-yl)benzamide (1449715-37-0)

Guidance literature:

With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 1h;

Reference yield:

4-(phenylethynyl)benzaldehyde (57341-98-7) → 3-((2S,5R)-4-oxo-5-(2-oxo-2-((2-(3-ethoxy-4-methoxyphenyl)(2H4)ethyl)amino)ethyl)-2-(4-((phenyl)ethynyl)phenyl)thiazolidin-3-yl)benzamide (1449715-37-0)

Guidance literature:

Multi-step reaction with 5 steps

1: acetonitrile / 72 h / 83 °C

2: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran; methanol / 70 °C

3: N-ethyl-N,N-diisopropylamine; diphenyl phosphoryl azide / toluene / 5 h / 100 °C

4: trifluoroacetic acid / dichloromethane / 20 °C

5: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / dichloromethane / 1 h / 20 °C

With diphenyl phosphoryl azide; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile;

Reference yield:

2-((2S,5S)-3-(3-carbamoylphenyl)-4-oxo-2-(4-(phenylethynyl)phenyl)thiazolidin-5-yl)acetic acid (1449715-38-1) → 3-((2S,5R)-4-oxo-5-(2-oxo-2-((2-(3-ethoxy-4-methoxyphenyl)(2H4)ethyl)amino)ethyl)-2-(4-((phenyl)ethynyl)phenyl)thiazolidin-3-yl)benzamide (1449715-37-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran; methanol / 70 °C

2: N-ethyl-N,N-diisopropylamine; diphenyl phosphoryl azide / toluene / 5 h / 100 °C

3: trifluoroacetic acid / dichloromethane / 20 °C

4: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / dichloromethane / 1 h / 20 °C

With diphenyl phosphoryl azide; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; toluene;

upstream raw materials:

4-(phenylethynyl)benzaldehyde

3-Aminobenzamide

2-((2S,5S)-3-(3-carbamoylphenyl)-4-oxo-2-(4-(phenylethynyl)phenyl)thiazolidin-5-yl)acetic acid

2-((2S,5R)-3-(3-carbamoylphenyl)-4-oxo-2-(4-(phenylethynyl)phenyl)thiazolidin-5-yl)acetic acid

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