(R,Z)-2-(3-((3-carboxy-N-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenyl)propanamido)methyl)benzamido)pentanedioic acid

Base Information

• Chemical Name: (R,Z)-2-(3-((3-carboxy-N-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenyl)propanamido)methyl)benzamido)pentanedioic acid
• CAS No.: 1310744-97-8
• Molecular Formula: C₂₇H₂₅N₃O₁₀S
• Molecular Weight: 583.576
• Mol file: 1310744-97-8.mol

Synonyms:

Chemical Property of (R,Z)-2-(3-((3-carboxy-N-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenyl)propanamido)methyl)benzamido)pentanedioic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R,Z)-2-(3-((3-carboxy-N-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenyl)propanamido)methyl)benzamido)pentanedioic acid

There total 7 articles about (R,Z)-2-(3-((3-carboxy-N-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenyl)propanamido)methyl)benzamido)pentanedioic acid 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: 27.0%

(R,Z)-dimethyl 2-(3-((N-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenyl)-4-methoxy-4-oxobutanamido)methyl)benzamido)pentanedioate (1310744-91-2) → (R,Z)-2-(3-((3-carboxy-N-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenyl)propanamido)methyl)benzamido)pentanedioic acid (1310744-97-8)

Guidance literature:

(R,Z)-dimethyl 2-(3-((N-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenyl)-4-methoxy-4-oxobutanamido)methyl)benzamido)pentanedioate; With lithium hydroxide; In methanol; water; at 20 ℃; for 16h;

With hydrogenchloride; In methanol; water;

DOI:10.1021/jm2002525

Reference yield:

(R,Z)-dimethyl 2-(3-((4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenylamino)methyl)benzamido)pentanedioate (1243277-47-5) → (R,Z)-2-(3-((3-carboxy-N-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenyl)propanamido)methyl)benzamido)pentanedioic acid (1310744-97-8)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / 24 h / 0 - 20 °C

2: lithium hydroxide / methanol; water / 16 h / 20 °C

With triethylamine; lithium hydroxide; In methanol; water;

DOI:10.1021/jm2002525

Reference yield:

(5Z)-5-(4-aminobenzylidene)-1,3-thiazolidine-2,4-dione (103754-57-0) → (R,Z)-2-(3-((3-carboxy-N-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenyl)propanamido)methyl)benzamido)pentanedioic acid (1310744-97-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: acetic acid / methanol / 1 h / 65 °C

1.2: 20 h / 20 °C / Inert atmosphere

2.1: triethylamine / 24 h / 0 - 20 °C

3.1: lithium hydroxide / methanol; water / 16 h / 20 °C

With acetic acid; triethylamine; lithium hydroxide; In methanol; water;

DOI:10.1021/jm2002525

upstream raw materials:

(R,Z)-dimethyl 2-(3-((4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenylamino)methyl)benzamido)pentanedioate

(R,Z)-dimethyl 2-(3-((N-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenyl)-4-methoxy-4-oxobutanamido)methyl)benzamido)pentanedioate

(5Z)-5-(4-aminobenzylidene)-1,3-thiazolidine-2,4-dione

m-formylphenyl benzoic acid

Refernces