1H-Pyrrole-2,4-dicarboxylic acid, 1-(2-hydroxyethyl)-5-(2-methoxy-2-oxoethyl)-3-(trifluoromethyl)-, 4-methyl 2-(phenylmethyl) ester

Base Information

• Chemical Name: 1H-Pyrrole-2,4-dicarboxylic acid, 1-(2-hydroxyethyl)-5-(2-methoxy-2-oxoethyl)-3-(trifluoromethyl)-, 4-methyl 2-(phenylmethyl) ester
• CAS No.: 783350-01-6
• Molecular Formula: C20H20F3NO7
• Molecular Weight: 443.377
• Mol file: 783350-01-6.mol

Synonyms:

Chemical Property of 1H-Pyrrole-2,4-dicarboxylic acid, 1-(2-hydroxyethyl)-5-(2-methoxy-2-oxoethyl)-3-(trifluoromethyl)-, 4-methyl 2-(phenylmethyl) ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1H-Pyrrole-2,4-dicarboxylic acid, 1-(2-hydroxyethyl)-5-(2-methoxy-2-oxoethyl)-3-(trifluoromethyl)-, 4-methyl 2-(phenylmethyl) ester

There total 2 articles about 1H-Pyrrole-2,4-dicarboxylic acid, 1-(2-hydroxyethyl)-5-(2-methoxy-2-oxoethyl)-3-(trifluoromethyl)-, 4-methyl 2-(phenylmethyl) 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: 91.0%

5-benzyloxycarbonyl-3-methoxycarbonyl-4-trifluoromethyl-1-(tetrahydropyranyloxyethyl)pyrrole-2-acetic acid methyl ester (783350-00-5) → 5-benzyloxycarbonyl-3-methoxycarbonyl-4-trifluoromethyl-1-(ω-hydroxyethyl)pyrrole-2-acetic acid methyl ester (783350-01-6)

Guidance literature:

With acetic acid; In water; at 55 - 60 ℃; for 1.75h;

DOI:10.3987/com-04-10124

Reference yield:

3-methoxycarbonyl-4-trifluoromethyl-5-benzyloxycarbonylpyrrole-2-acetic acid methyl ester → 5-benzyloxycarbonyl-3-methoxycarbonyl-4-trifluoromethyl-1-(ω-hydroxyethyl)pyrrole-2-acetic acid methyl ester (783350-01-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / K₂CO₃; NaI / dimethylformamide / 2 h / 95 °C

2: 91 percent / AcOH / H₂O / 1.75 h / 55 - 60 °C

With potassium carbonate; acetic acid; sodium iodide; In water; N,N-dimethyl-formamide;

DOI:10.3987/com-04-10124

Reference yield:

5-benzyloxycarbonyl-3-methoxycarbonyl-4-trifluoromethyl-1-(ω-hydroxyethyl)pyrrole-2-acetic acid methyl ester (783350-01-6) → 5-benzoyl-6-trifluoromethyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid

Guidance literature:

Multi-step reaction with 8 steps

1.1: Et₃N / CH₂Cl₂ / 1 h / 20 °C

2.1: 20.80 g / NaH / dimethylformamide / 0.5 h / 20 °C

3.1: 100 percent / H₂ / Pd/C / ethyl acetate / 2 h

4.1: oxalyl chloride / toluene / 2 h / Heating

4.2: 54 percent / iron(III) acetylacetonate / tetrahydrofuran / 0.33 h

5.1: 67 percent / HMPA; lithium thioethoxide

6.1: 75 percent / HCl gas / 2 h / 20 °C

7.1: 53 percent / quinoline; CuO / 0.25 h / 215 °C

8.1: 78 percent / MeSO₃H; HCO₂H / 16 h / 55 °C

With quinoline; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; formic acid; oxalyl dichloride; methanesulfonic acid; hydrogen; sodium hydride; lithium thioethoxide; triethylamine; copper(II) oxide; palladium on activated charcoal; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.3987/com-04-10124

upstream raw materials:

5-benzyloxycarbonyl-3-methoxycarbonyl-4-trifluoromethyl-1-(tetrahydropyranyloxyethyl)pyrrole-2-acetic acid methyl ester

Downstream raw materials:

5-benzoyl-6-trifluoromethyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid isopropyl ester

1,7-dimethoxycarbonyl-5-benzoyl-6-trifluoromethyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole

5-benzoyl-6-trifluoromethyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1,7-dicarboxylic acid

1,7-dimethoxycarbonyl-5-benzyloxycarbonyl-6-trifluoromethyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole